JPH11322710A - Acrylonitrile compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new acrylonitrile compound capable of manifesting an excellent pest controlling activity with a small dose, scarcely adversely affecting nontarget organisms such as mammals, fishes and beneficial insects, having high safety and useful as agrochemicals. SOLUTION: This compound is represented by formula I Q is a (substituted) phenyl, a (substituted)naphthyl or a (substituted)heterocyclic ring; B is a halogen, S(O)n L<1> [L<1> is H, a (substituted) 1-4C alkyl or the like; (n) is 0, l or 2] or the like; A is a (substituted)phenyl, a (substituted)naphthyl or a (substituted) heterocyclic ring]}, e.g. 2-(4-tertiary butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4- yl)-3-chloroacrylonitrile. The compound represented by formula I is preferably obtained by reacting, e.g. a compound represented by formula II (B' is a halogen or the like) with a thioalcoholate represented by the formula L<1> -SNa and further reacting the resultant compound with an oxidizing agent such as aqueous hydrogen peroxide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel acrylonitrile compound and an agrochemical containing the compound as an active ingredient. The pesticides in the present invention are insecticides, acaricides, nematicides, herbicides, fungicides, and the like, and are particularly pesticides, acaricides, and nematicides in the fields of agriculture, horticulture, livestock, and sanitation. .

[0002]

2. Description of the Related Art For acrylonitrile derivatives, 3
-Bromo-2,3-diphenyl derivative is disclosed in
8569, a 3- (methylthio) -2,3-diphenylacrylonitrile derivative was added to Chemische Berichte 10
Vol. 0, No. 5, page 1413 1967 {Chem. B
er. , 100 (5), 1413 (1967)}, and a 3- (pyridylamino) -2- (1H-tetrazolyl-5-yl) -acrylonitrile derivative as described in WO-93 /
16070.

[0003]

With the long-term use of insecticides and fungicides, pests have recently acquired resistance,
Control with conventional insecticides and fungicides has become difficult.
Some insecticides are highly toxic, and some are persisting in ecosystems due to persistence. Therefore, an object of the present invention is to provide a novel insecticide or fungicide with low toxicity and low residual.

[0004]

In order to solve the above-mentioned problems, the present inventors have demonstrated excellent pest control activity at a low dose, and have been applied to non-target organisms such as mammals, fish and beneficial insects. As a result of continuing research to develop a pesticide having almost no adverse effects, the present inventors have found that the following compounds have high safety and excellent pesticidal activity and completed the present invention. That is, the present invention relates to the compounds described in the following [1] to [6] (hereinafter, referred to as the present compounds) and pesticides containing the compounds as active ingredients.

[1] Equation (1):

[0006]

Embedded image

Wherein Q may be substituted with G
Phenyl, naphthyl optionally substituted with G or R
A heterocyclic group which may be substituted with
Is thienyl, furyl, pyrrolyl, oxazolyl, iso
Xazolyl, thiazolyl, isothiazolyl, pyrazoly
, Imidazolyl, 1,3,4-oxadiazolyl,
1,2,4-oxadiazolyl, 1,3,4-thiadia
Zolyl, 1,2,4-thiadiazolyl, 1,2,4-to
Liazolyl, 1,2,3-thiadiazolyl, 1,2,3
-Triazolyl, 1,2,3,4-tetrazolyl, pyri
Dinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
1,3,5-triazinyl, 1,2,4-triazinyl
1,2,4,5-tetrazinyl, pyrazolinyl, i
Midazolinyl, oxazolinyl, isoxazolinyl,
Azolinyl, imidazolinone, imidazolidinedione,
3 (2H) -pyridazinone, benzothiazolyl, benzo
Imidazolyl, indazolyl, benzoxazolyl,
Nolinyl, isoquinolinyl, quinoxalinyl, phthalazi
Nyl, cinnolinyl or quinazolinyl. )
B is halogen, S (O) nL¹Or NL^TwoL^Threeso
A is phenyl optionally substituted with W,
Optionally substituted with naphthyl or Y
A heterocyclic group (provided that the heterocyclic group is thienyl,
Ryl, pyrrolyl, oxazolyl, isoxazolyl, thia
Zolyl, isothiazolyl, pyrazolyl, imidazolyl,
1,3,4-oxadiazolyl, 1,2,4-oxadi
Azolyl, 1,3,4-thiadiazolyl, 1,2,4-
Thiadiazolyl, 1,2,4-triazolyl, 1,2,2
3-thiadiazolyl, 1,2,3-triazolyl, 1,
2,3,4-tetrazolyl, pyridinyl, pyrimidiny
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, pyrazolinyl, imi
Dazolinyl, oxazolinyl, isoxazolinyl, thia
Zolinyl, 3 (2H) -pyridazinone, benzothiazoly
, Benzimidazolyl, indazolyl, benzoxa
Zolyl, quinolinyl, isoquinolinyl, quinoxalini
, Phthalazinyl, cinnolinyl or quinazolinyl
is there. ) Where (a) B is NL^TwoL^ThreeIs
First, Q is 1,2,3,4-te which may be substituted by R.
Tolazolyl, quinolyl optionally substituted with R, or
In the case of isoquinolyl optionally substituted with R, A is
Naphthyl optionally substituted with W or substituted with Y
An optionally substituted heterocyclic group (this heterocyclic group may be thienyl,
, Pyrrolyl, oxazolyl, isoxazolyl, thiazo
Ryl, isothiazolyl, pyrazolyl, imidazolyl,
1,3,4-oxadiazolyl, 1,2,4-oxadi
Azolyl, 1,3,4-thiadiazolyl, 1,2,4-
Thiadiazolyl, 1,2,4-triazolyl, 1,2,2
3-thiadiazolyl, 1,2,3-triazolyl, pyri
Dinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
1,3,5-triazinyl, 1,2,4-triazinyl
, Pyrazolinyl, imidazolinyl, oxazolinyl,
Isoxazolinyl, thiazolinyl, 3 (2H) -pyrida
Zinone, benzothiazolyl, benzimidazolyl, inn
Dazolyl, benzoxazolyl, quinolinyl, isoquino
Linyl, quinoxalinyl, phthalazinyl, cinnolinyl
Or quinazolinyl. ) And (b) B is S
(O) nL¹And Q may be substituted with R
Benzothiazolyl, A is substituted with W
Phenyl, naphthyl optionally substituted with W,
Or a heterocyclic group optionally substituted with Y (this heterocyclic group
Are thienyl, furyl, pyrrolyl, oxazolyl,
Sazolyl, thiazolyl, isothiazolyl, pyrazolyl,
Imidazolyl, 1,2,4-triazolyl, 1,2,3
-Triazolyl, 1,2,3,4-tetrazolyl, pyri
Dinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
1,3,5-triazinyl, 1,2,4-triazinyl
, Pyrazolinyl, imidazolinyl, oxazolinyl,
Isoxazolinyl, thiazolinyl, 3 (2H) -pyrida
Zinone, benzothiazolyl, benzimidazolyl, inn
Dazolyl, quinolinyl, isoquinolinyl, quinoxalini
, Phthalazinyl, cinnolinyl or quinazolinyl
is there. (C) B is halogen, S (O) nL¹Ma
Or NL^TwoL^ThreeAnd Q may be replaced by G
A is a phenyl which may be substituted by W
A heterocyclic group which may be substituted with
Heterocyclic groups are pyrrolyl, oxazolyl, isoxazolyl,
Thiazolyl, isothiazolyl, pyrazolyl, 1,3,4
-Oxadiazolyl, 1,2,4-oxadiazolyl,
1,3,4-thiadiazolyl, 1,2,4-thiadiazo
Ryl, 1,2,4-triazolyl, 1,2,3-thiazi
Azolyl, 1,2,3-triazolyl, 1,2,3,4
-Tetrazolyl, pyrazinyl, pyridazinyl, 1,3,
5-triazinyl, 1,2,4-triazinyl, pyrazo
Linyl, imidazolinyl, oxazolinyl, isoxazo
Linyl, thiazolinyl, 3 (2H) -pyridazinone,
Nzothiazolyl, benzimidazolyl, indazolyl,
Benzoxazolyl, quinoxalinyl, phthalazinyl,
Cinolinyl or quinazolinyl. ) And L
¹Is H, C₁~ C_FourAlkyl, C_Two~_FourAlkenyl, C_Two~
_FourAlkynyl, C₁~ C_ThreeMay be substituted with alkyl
C_Three~ C₆Cycloalkyl, C₁~ C_FourHaloalkyl, C
H_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, Substituted with Z
Phenyl, C substituted with Ra₁~ C_FourArchi
, C substituted with Rb₁~ C_FourAlkyl, tetrahydro
Pyranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfe
Nil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourArchi
Rusulfonyl, halogen or C₁~ C_FourAlkyl
Optionally substituted phenylsulfenyl and halogen
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Rusulfinyl, halogen or C₁~ C_FourWith alkyl
Optionally substituted phenylsulfonyl, -SO _TwoC
F_Three, C₁~ C_FourMonoalkylaminosulfonyl, C_Two~ C
₈Dialkylaminosulfonyl, phenylaminosulfo
Nil, C_Two~ C_FiveMonoalkylaminothiocarbonyl, C
_Three~ C₉Dialkylaminothiocarbonyl, C_Two~ C_FiveSheer
Noalkyl, C _Three~ C₉Alkoxycarbonylalkyl,
-C (O) T¹, -P (O) T^TwoT^Three, -P (S) T
^TwoT^Three, Alkali metal, alkaline earth metal or NHT^FourT
^FiveT⁶And L^TwoAnd L^ThreeAre each independently H, C₁~ C_Four
Alkyl, C_Two~ C_FourAlkenyl, C _Two~ C_FourAlkynyl,
C₁~ C_ThreeC optionally substituted with an alkyl group_Three~ C₆Shi
Chloroalkyl, C₁~ C_FourHaloalkyl, C_Two~ C_FourArco
Xyalkyl, CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two,
Phenyl optionally substituted with Z, substituted with Ra
C₁~ C_FourAlkyl, C substituted with Rb₁~ C_FourArchi
, Tetrahydropyranyl, (CH_Three)_ThreeSi, C₁~ C_Four
Alkylsulfonyl, halogen or C₁~ C_FourArchi
Phenylsulfonyl optionally substituted with
_TwoCF_Three, C₁~ C_FourMonoalkylaminosulfonyl, C_Two
~ C₈Dialkylaminosulfonyl, phenylaminos
Ruphonyl, C_Two~ C_FiveMonoalkylaminothiocarboni
Le, C_Three~ C₉Dialkylaminothiocarbonyl, C_Two~
C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonyla
Lucil, -C (O) T¹, -P (O) T^TwoT^Three, -P
(S) T^TwoT^Three, Alkali metal, alkaline earth metal or
NHT^FourT^FiveT⁶Or L^TwoAnd L^ThreeThis
Oxygen and nitrogen atoms together with the nitrogen atom
Or a 5- to 8-membered ring group optionally containing a sulfur atom.
G may be halogen, C₁~ C_TenArchi
Le, C_Two~ C_FourCyanoalkyl, C substituted with Ra₁~ C
_FourAlkyl, C_Two~ C₆Alkenyl, C_Two~ C₆Alkini
Le, C₁~ C₆Haloalkyl, C_Two~ C₆Haloalkenyl,
C_Two~ C₆Haloalkynyl, C_Three~ C₆Halocycloalkyl
Le, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆
Cycloalkyl, C₁~ C_TenAlkoxy, C_Two~ C₆Al
Kenyloxy, C_Two~ C₆Alkynyloxy, C₁~ C_FourC
Lower alkoxy, C_Two~ C₆Haloalkenyloxy, C_Two~
C₆Haloalkynyloxy, C₁~ C_FourAlkylsulfe
Nil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourArchi
Rusulfonyl, C_Two~ C₆Alkenylsulfenyl, C_Two
~ C₆Alkenylsulfinyl, C_Two~ C₆Alkenyls
Ruphonyl, C_Two~ C₆Alkynylsulfenyl, C_Two~ C₆
Alkynylsulfinyl, C_Two~ C₆Alkynylsulfoni
Le, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHalo
Alkylsulfinyl, C₁~ C_FourHaloalkylsulfoni
Le, C_Two~ C₆Haloalkenylsulfenyl, C_Two~ C₆C
Loalkenylsulfinyl, C_Two~ C₆Haloalkenyls
Ruphonyl, C_Two~ C₆Haloalkynylsulfenyl, C_Two
~ C₆Haloalkynylsulfinyl, C_Two~ C₆Haloal
Quinylsulfonyl, CHO, NO_Two, CN, -NU¹U^Two,
OH, naphthyl, methoxy substituted with Ra, C_Two~ C₇
Alkoxycarbonyl, C_Two~ C _FourAlkoxyalkyl,
C_Two~ C_FourAlkylcarbonyl, C_Two~ C_FourHaloalkyl mosquito
Rubonil, C_Two~ C_FiveAlkylcarbonyloxy, C_Two~
C_FiveHaloalkylcarbonyloxy, C_Three~ C₇Dialki
Aminocarbonyloxy, optionally substituted with Z
Phenyl, phenoxy optionally substituted with Z,
Optionally substituted benzoyl, substituted with Z
Pyridyl, pyridylo optionally substituted with Z
Xy, thienyl optionally substituted with Z, adjacent positions
Methylenedioxy linked at substitution positions, adjacent substitution positions
Halomethylenedioxy and -N = CT⁷T
⁸(However, T⁷And T⁸Are each independently H, phenyl,
Oil or C₁~ C₆Alkyl or T⁷And T⁸And
Form a 5- to 8-membered ring with the carbon atoms
Is also good. 1) to 4 substituents selected from
Or by an alkylene group attached at an adjacent substitution position
A 5- to 8-membered ring formed wherein R is halogen, C
₁~ C_TenAlkyl, C substituted with Ra₁~ C_FourAlkyl,
C _Two~ C₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆
Haloalkyl, C_Two~ C₆Haloalkenyl, C_Two~ C₆Halo
Alkynyl, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeA
C optionally substituted with alkyl_Three~ C₆Cycloalkyl
Le, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy,
C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy,
C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Halo alkini
Luoxy, C ₁~ C_FourAlkylsulfenyl, C₁~ C_FourA
Rukylsulfinyl, C₁~ C_FourAlkylsulfonyl, C
_Two~ C₆Alkenylsulfenyl, C_Two~ C₆Alkenyls
Rufinil, C_Two~ C₆Alkenylsulfonyl, C_Two~ C₆
Alkynylsulfenyl, C_Two~ C₆Alkynyl sulf
Inil, C_Two~ C₆Alkynylsulfonyl, C₁~ C_FourHalo
Alkylsulfenyl, C₁~ C_FourHaloalkyl sulfy
Nil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆Halo
Alkenylsulfenyl, C_Two~ C₆Haloalkenylsul
Finil, C_Two~ C₆Haloalkenylsulfonyl, C_Two~
C₆Haloalkynylsulfenyl, C_Two~ C₆Haloalk
Nilsulfinyl, C_Two~ C₆Haloalkynylsulfoni
Le, NO_Two, CN, -NU¹U^Two, Phenoxy, OH, na
Futyl, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourAl
Coxyalkyl, C_Two~ C_FourAlkylcarbonyl, C_Two~
C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloalkyl
Carbonyloxy, benzoi optionally substituted by X
Phenyl optionally substituted with X, substituted with X
Optionally substituted pyridyl, X-substituted chie
Nil and -N = CT⁷T⁸1 to 4 pieces selected from
Or an alkylene bonded at an adjacent substituent position
A 5- to 8-membered ring formed by a
Halogen, C₁~ C_TenAlkyl, C₁~ C₆Haloalk
Le, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy,
C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy,
C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Halo alkini
Luoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourA
Rukylsulfinyl, C₁~ C_FourAlkylsulfonyl, C
_Two~ C₆Alkenylsulfenyl, C_Two~ C₆Alkenyls
Rufinil, C_Two~ C₆Alkenylsulfonyl, C_Two~ C₆
Alkynylsulfenyl, C _Two~ C₆Alkynyl sulfy
Nil, C_Two~ C₆Alkynylsulfonyl, C₁~ C_FourHaloa
Rukylsulfenyl, C₁~ C_FourHaloalkylsulfini
Le, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆Haloa
Lucenylsulfenyl, C_Two~ C₆Haloalkenyl sulf
Inil, C_Two~ C₆Haloalkenylsulfonyl, C_Two~ C₆
Haloalkynylsulfenyl, C_Two~ C₆Haloalkynyl
Sulfinyl, C_Two~ C₆Haloalkynylsulfonyl, N
O_Two, CN, -NU¹U^Two, OH, C_Two~ C₇Alkoxycal
Bonil, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FiveArchi
Lecarbonyloxy, C_Two~ C_FiveHaloalkylcarbonyl
Oxy, C_Three~ C₇Dialkylaminocarbonyloxy,
Phenyl optionally substituted with X, and -N = CT⁷
T⁸(However, T⁷And T⁸Is each independently H, phenyl,
Benzyl or C₁~ C₆Alkyl or T⁷And T⁸When
Forms a 5- to 8-membered ring with the carbon atom to which they are attached
You may. 1) to 4 substituents selected from
Or an alkylene group bonded at an adjacent
A 5- to 8-membered ring formed by W is halogen,
C₁~ C₆Alkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourA
Lucoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkyl
Sulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~
C_FourAlkylsulfonyl, C₁~ C_FourHaloalkyl sulf
Enil, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_Four
Haloalkylsulfonyl, C_Two~ C_FourAlkenyl, C_Two~
C_FourHaloalkenyl, C_Two~ C_FourAlkenyloxy, C_Two~
C_FourHaloalkenyloxy, C_Two~ C_FourAlkenyl sulf
Enil, C_Two~ C_FourAlkenylsulfinyl, C_Two~ C_FourA
Lucenylsulfonyl, C_Two~ C_FourHaloalkenyl sulfe
Nil, C_Two~ C_FourHaloalkenylsulfinyl, C_Two~ C_Four
Haloalkenylsulfonyl, C_Two~ C_FourAlkynyl, C_Two
~ C_FourHaloalkynyl, C_Two~ C_FourAlkynyloxy, C_Two
~ C_FourHaloalkynyloxy, C_Two~ C_FourAlkynylsul
Phenyl, C_Two~ C_FourAlkynylsulfinyl, C_Two~ C_Four
Alkynylsulfonyl, C_Two~ C_FourHaloalkynylsulf
Enil, C_Two~ C_FourHaloalkynylsulfinyl, C_Two~
C_FourHaloalkynylsulfonyl, NO_Two, CN, Holmi
Le, C_Two~ C₆Alkoxycarbonyl, C_Two~ C₆Alkyl
Carbonyl, C_Two~ C₆Haloalkylcarbonyl, C_Two~
C₆Alkylcarbonyloxy and -NU¹U^TwoFrom within
1 to 5 substituents selected,¹Is hydrogen,
C₁~ C₂₀Alkyl, C_Two~ C₆Alkenyl, C₁~ C₆C
Lower alkyl, C₁~ C_FourAlkoxy-C₁~ C_FourAlkyl,
C_Three~ C₆Halocycloalkyl, C substituted with Ra₁~ C
_FourAlkyl, C₁~ C_ThreeOptionally substituted with alkyl
C_Three~ C₆Cycloalkyl, cycloal substituted with Ra
Kill, Ra and C₁~ C_FourCyclopropyl substituted with alkyl
Ropyl, Rc and halogen-substituted C_Three~ C_FourCyclo
Alkyl group, Rd and C₁~ C_FourAlkyl-substituted
Chloropropyl group, C substituted by Ra_Two~ C_FourAlkene
Le, C₁~ C₁₂Alkoxy, C₁~ C_FourHaloalkoxy,
C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeSubstituted with alkyl
C that may be_Three~ C₆Cycloalkoxy, benzylo
Kissi, C_Two~ C_FiveAlkoxycarbonyl, -NU¹U^Two,
Phenylamino, phenyl optionally substituted with Z, Z
Optionally substituted with phenoxy, substituted with Z
Phenylthio, naph optionally substituted with Z
A heterocyclic group optionally substituted with tyl or Z (provided that
These heterocyclic groups are thienyl, furyl, pyrrolyl, oxo
Sazolyl, isoxazolyl, thiazolyl, isothiazoly
, Pyrazolyl, imidazolyl, 1,3,4-oxadi
Azolyl, 1,2,4-oxadiazolyl, 1,3,4
Thiadiazolyl, 1,2,4-thiadiazolyl, 1,
2,4-triazolyl, 1,2,3-thiadiazolyl,
1,2,3-triazolyl, 1,2,3,4-tetrazo
Lil, pyridinyl, pyrimidinyl, pyrazinyl, pyrida
Zinyl, 1,3,5-triazinyl, 1,2,4-tri
Azinyl, pyrazolinyl, imidazolinyl, oxazoly
Nil, isoxazolinyl, thiazolinyl and 3 (2H)
-Selected from among pyridazinones; ) And T^Twoas well as
T^ThreeIs independently OH, phenyl, C₁~ C₆Archi
Le, C₁~ C₆Alkoxy or C₁~ C_FourAlkylsulf
And T^Four, T^FiveAnd T⁶Are each independently H, C₁
~ C₆Alkyl, C₁~ C₆Alkenyl, C₁~ C_ThreeArchi
C which may be substituted with_Three~ C₆Cycloalkyl group
Or benzyl, or T^Four, T^FiveAnd T⁶of
Two of them, together with the nitrogen atom to which each is attached
Even if it contains oxygen, nitrogen or sulfur atoms
X and Z may form a good 5- to 8-membered ring group.
Each independently represents halogen, C₁~ C_FourAlkyl, C₁~ C_Four
Haloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloal
Coxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAl
Killsulfinyl, C₁~ C_FourAlkylsulfonyl, C_Two
~ C_FiveAlkenylsulfenyl, C_Two~ C_FiveAlkenyls
Rufinil, C_Two~ C_FiveAlkenylsulfonyl, C₁~ C_Four
Haloalkylsulfenyl, C₁~ C_FourHaloalkylsul
Finil, C₁~ C_FourHaloalkylsulfonyl, NO_Two,
CN, CHO, OH, -NU¹U^Two, Phenyl, phenoki
Si and C_Two~ C_FiveSelected from among alkoxycarbonyl
1 to 5 substituents,⁷And T⁸Are independent
, H, phenyl, benzyl or C₁~ C₆With alkyl
Is or T⁷And T⁸The carbon atom to which is bound
May form a 5- to 8-membered ring together with¹And U
^TwoIs independently H, C₁~ C₆Alkyl, C_Two~ C_FiveA
Represents alkylcarbonyl, phenyl or benzyl, or
U¹And U^Two5 to 8 members together with the carbon atom to which
May form a ring, n is 0, 1 or 2;
a is halogen and C₁~ C_FourOne selected from alkyl
Phenyl which may be substituted as described above, and Rb represents halo
Gen and C₁~ C_FourSubstituted with one or more selected from alkyl
Benzoyl, wherein R c is halogen and
C₁~ C_FourSubstituted with one or more kinds selected from alkoxy
Rd is substituted with halogen.
Good C_Two~ C_FourAlkenyl. Acry expressed by]
Lonitrile compounds.

[2] The acrylonitrile compound according to [1], wherein Q is phenyl optionally substituted with G, thiazolyl optionally substituted with R, or pyrazolyl optionally substituted with R. [3] The acrylonitrile compound according to [1], wherein Q is phenyl optionally substituted with G.

[4] The acrylonitrile compound according to [1], wherein Q is thiazolyl optionally substituted with R.
[5] The acrylonitrile compound according to [1], wherein Q is pyrazolyl optionally substituted with R. [6] [1]
A pesticide comprising as an active ingredient at least one of the acrylonitrile compounds according to items [5] to [5].

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION -C (C
The N) = C (B)-moiety has two isomers, E-form and Z-form, both of which are included in the present invention. When the substituent B in the formula (1) is —SH and NHL ² , the compound of the present invention has the formula

[0011]

Embedded image

It will be understood that they may exist in tautomeric forms represented by The compound is thought to exist predominantly in (1 '), but under certain conditions the tautomeric form (2)
Can be taken. It is to be understood that the present invention includes all three tautomeric forms and mixtures thereof.

Next, Q, A, B, G, R, L ¹ , L ² ,
L ³ , Y, Y ¹ , Y ² , W, X, Z, T ¹ , T ² , T ³ ,
Preferred ranges of T ⁴ , T ⁵ , T ⁶ , T ⁷ , T ⁸ , U ¹ , U ² and n will be described. However, no less QI to QV, AI to heterocyclic groups in AV, and T ¹ I to T ¹ III represent the following meanings. That is, thienyl is a thiophen-2-yl group or a thiophen-3-yl group, furyl is a furan-2-yl group or a furan-3-yl group, and pyrrolyl is a pyrrol-1-yl group, a pyrol-1-yl group. -Ru-2-yl group,
A pyrrol-3-yl group, oxazolyl is an oxazol-2-yl group, oxazol-4-yl group or oxazol-5-yl group, and thiazolyl is a thiazol-2-yl group, thiazol-4-yl group. Or thiazol-5-yl group, imidazolyl is imidazol-1-yl group, imidazol-2-yl group or imidazol-4-yl group, and isoxazolyl isoxazol-3-yl group, isoxazol-4-yl group. Or isoxazol-5-yl group, and isothiazolyl is isothiazol-3-yl group, isothiazol-4-yl group.
Yl or isothiazol-5-yl; pyrazolyl is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl;
An yl group, and 1,3,4-oxadiazolyl is 1,
3,4-oxadiazol-2-yl group;
3,4-thiadiazolyl is a 1,3,4-thiadiazol-2-yl group, and 1,2,4-oxadiazolyl is a 1,2,4-oxadiazol-3-yl group or 1,
2,4-oxadiazol-5-yl group;
2,4-thiadiazolyl is a 1,2,4-thiadiazol-3-yl group or 1,2,4-thiadiazol-5
1,2,4-triazolyl is 1,2,4
-Triazol-1-yl group, 1,2,4-triazol-3-yl group or 1,2,4-triazol-4-
1,2,3-thiadiazolyl is 1,2,2
A 3-thiadiazol-4-yl group or a 1,2,3-thiadiazol-5-yl group, and 1,2,3-triazolyl is a 1,2,3-triazol-1-yl group;
2,3-triazol-2-yl group or 1,2,3-
1,2,3,4-tetrazolyl is a 1,2,3,4-tetrazol-1-yl group, 1,2,3,4-tetrazol-2-yl group or 1 , 2,3,4-tetrazol-5-yl group, pyridinyl is a pyridin-2-yl group, pyridin-3-yl group or pyridin-4-yl group, pyrimidinyl is a pyrimidin-2-yl group, A pyrimidin-4-yl group or a pyrimidin-5-yl group, pyrazinyl is a pyrazin-2-yl group, and pyridazinyl is a pyridazin-3
-Yl group or pyridazin-4-yl group,
3,5-triazinyl is 1,3,5-triazine-2-
1,2,4-triazinyl is 1,2,4
-Triazin-3-yl group, 1,2,4-triazine-
5-yl group or 1,2,4-triazin-6-yl group, and 1,2,4,5-tetrazinyl is 1,2,4
5-tetrazin-3-yl group, pyrazolinyl is 3
-Pyrazolin-1-yl group, 3-pyrazolin-3-yl group, 3-pyrazolin-4-yl group or 3-pyrazolin-5-yl group, and imidazolinyl is 1-imidazolin-3-yl group, 1- Imidazolin-2-yl group, 1-
Imidazolin-4-yl group or 4-imidazoline-2
-Yl group, oxazolinyl is 2-oxazoline-
2-yl group, 2-oxazolin-4-yl group or 2-
An oxazolin-5-yl group, isoxazolinyl is a 2-isoxazolin-3-yl group, 2-isoxazolin-4-yl group or 2-isoxazolin-5-yl group, and thiazolinyl is a 2-thiazolin-2-yl group. , 2
-Thiazolin-4-yl group or 3-thiazolin-2-
An imidazolidinone-yl group, an imidazolidin-2-one-1-yl group, an imidazolinone-yl group is a 2-imidazolinone-1-yl group, and 3 (2
H) -Pyridazinone-yl is a 3 (2H) -pyridazinone-2-yl, 3 (2H) -pyridazinone-4-yl, 3 (2H) -pyridazinone-5-yl or 3
(2H) -Pyridazinone-6-yl group.

Preferred ranges of Q are the following groups. That is, QI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-
Oxadiazolyl, 1,2,4-oxadiazolyl,
1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4
-Tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,
2,4-triazinyl, 1,2,4,5-tetrazinyl.

QII: phenyl, thiazolyl, pyrazolyl. QIII: phenyl. QIV: thiazolyl. QV: pyrazolyl. Preferred ranges of A are the following groups. That is, A
I: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
Pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,2
4-triazolyl, 1,2,3-thiadiazolyl, 1,
2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl.

AII: phenyl, thiazolyl, pyrazolyl. AIII: Thiazolyl. AIV: pyrazolyl. AV: phenyl. Preferred ranges of B are the following groups. That is, B
I: halogen, S (O) nL ¹ , NL ² L ³ BII: halogen BIII: S (O) nL ¹ BIV: NL ²
L ^{3 The} preferred range of L ¹ is the following groups.

That is, L¹I: H, C₁~ C_FourAlkyl, C_Two
~ C_FourAlkenyl, C_Two~ C_FourAlkynyl, C¹~ C^ThreeAl
C optionally substituted with a kill group_Three~ C₆Cycloalkyl
Le, C₁~ C_FourHaloalkyl, C_Two~ C_FourAlkoxyalkyl
Le, CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, Replaced by Z
Optionally substituted phenyl, C substituted with Ra₁~ C_FourA
Alkyl, C substituted with Rb₁~ C_FourAlkyl, tetrahi
Dropyranil, (CH_Three) _ThreeSi, C₁~ C_FourAlkylsul
Honyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally phenylsulfonyl, -SO_TwoCF_Three, C₁
~ C_FourMonoalkylaminosulfonyl, C_Two~ C₈Gials
Killaminosulfonyl, phenylaminosulfonyl, C
_Two~ C_FiveMonoalkylaminothiocarbonyl, C_Three~ C₉The
Alkylaminothiocarbonyl, C_Two~ C_FiveCyano Archi
Le, C_Three~ C₉Alkoxycarbonylalkyl, -C
(O) T¹, -P (O) T^TwoT^Three, -P (S) T^TwoT^Three,
Lucari metal, alkaline earth metal or NHT^FourT^FiveT⁶.

L ¹ II: H, C ₁ -C ₄ alkyl, C ₂ -C ₄
Alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₃ alkyl substituted optionally C ₃ even though -C ₆ cycloalkyl, C ₁ ~
C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, phenyl optionally substituted by ^{Z, -C (O) T 1} , alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ^6. L ¹ III: H, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl,
C ₂ -C ₄ alkynyl, C ₁ -C ₃ optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, optionally substituted by Z phenyl, -C (O) T ^1.

Preferred L^TwoRange is for each group shown below.
You. That is, L^TwoI: H, C₁~ C_FourAlkyl, C_Two~ C_FourAl
Kenil, C_Two~ C_FourAlkynyl, C₁~ C_ThreeSubstitute with alkyl
C that may be_Three~ C₆Cycloalkyl, C₁~ C_FourC
Lower alkyl, C_Two~ C_FourAlkoxy, C_Two~_FourAlkoxya
Alkyl, phenyl optionally substituted by Z,
Transformed C₁~ C_FourAlkyl, C substituted with Rb₁~ C_Four
Alkyl, tetrahydropyranyl, (CH_Three)_ThreeSi, C
₁~ C_FourAlkylsulfonyl, halogen or C₁~ C_Four
Phenylsulfonyl optionally substituted with alkyl,
-SO_TwoCF_Three, C₁~ C_FourMonoalkylaminosulfoni
Le, C_Two~ C₈Dialkylaminosulfonyl, phenyla
Minosulfonyl, C_Two~ C_FiveMonoalkylaminothiocal
Bonil, C_Three~ C₉Dialkylaminothiocarbonyl, C
_Two~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonyl
Alkyl, -C (O) T ¹, -P (O) T^TwoT^Three, -P
(S) T^TwoT^Three, Alkali metal, alkaline earth metal or
NHT^FourT^FiveT⁶.

L ² II: H, C ₁ -C ₄ alkyl, C ₂ -C ₄
Alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, C ₂ ~
C ₄ alkoxyalkyl, phenyl optionally substituted by Z, C substituted with Ra ₁ -C ₄ alkyl ,, C ₂ -C
₅ mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, -C (O) T ¹ ,, alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ^6.

L ² III: H, C ₁ -C ₄ alkyl, C ₂ -C ₄
Alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, C ₂ ~
C ₄ alkoxyalkyl, optionally substituted by Z phenyl, -C (O) T ^1. L ² IV: L ² and L ³ may form a 5- to 8-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the bonded nitrogen atom.

Preferred L^ThreeRange is for each group shown below.
You. That is, L^ThreeI: H, C₁~ C_FourAlkyl, C_Two~ C_FourAl
Kenil, C_Two~ C_FourAlkynyl, C₁~ C_ThreeSubstitute with alkyl
C that may be_Three~ C₆Cycloalkyl, C₁~ C_FourC
Lower alkyl, C_Two~ C_FourAlkoxy, C_Two~ C_FourAlkoxy
Alkyl, phenyl optionally substituted with Z,
Replaced C₁~ C_FourAlkyl, C substituted with Rb₁~ C
_FourAlkyl, tetrahydropyranyl, (CH_Three)_ThreeSi,
C₁~ C_FourAlkylsulfonyl, halogen or C₁~
C_FourPhenylsulfoni optionally substituted with alkyl
, -SO_TwoCF_Three, C₁~ C_FourMonoalkylamino sulfo
Nil, C _Two~ C₈Dialkylaminosulfonyl, phenyl
Aminosulfonyl, C_Two~ C_FiveMonoalkylaminothioca
Rubonil, C_Three~ C₉Dialkylaminothiocarbonyl,
C _Two~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarboni
Alkyl, -C (O) T ¹, -P (O) T^TwoT^Three, -P
(S) T^TwoT^Three, Alkali metal, alkaline earth metal or
NHT^FourT^FiveT⁶.

L ³ II: H, C ₁ -C ₄ alkyl, C ₂ -C ₄
Alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, C ₂ ~
C ₄ alkoxyalkyl, phenyl optionally substituted by Z, C ₁ -C ₄ alkyl substituted by Ra, C ₂ -C ₅
Mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, -C (O) T ¹ ,, alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ^6.

L^ThreeIII: H, C₁~ C_FourAlkyl, C_Two~ C_Four
Alkenyl, C_Two~ C_FourAlkynyl, C₁~ C_ThreeWith alkyl
Optionally substituted C_Three~ C₆Cycloalkyl, C_Two~
C_FourAlkoxyalkyl, a group optionally substituted with Z
Enyl, -C (O) T¹. Preferred ranges of G are the following groups. That is, G
I: halogen, C₁~ C₆Alkyl, C_Two~ C_FourAlkene
Le, C_Two~ C_FourAlkynyl, C₁~ C_FourHaloalkyl, C_Two
~ C_FourHaloalkenyl, C_Two~ C_FourHaloalkynyl, C₁~
C_ThreeC3-C6 cycloalkyl optionally substituted with alkyl
Luquil, C ₁~ C₆Alkoxy, C_Two~ C_FourAlkenyloxy
Si, C_Two~ C_FourAlkynyloxy, C ₁~ C_FourHaloalkoki
Si, C_Two~ C_FourHaloalkenyloxy, C_Two~ C_FourHaloal
Quinyloxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C ₁~ C_FourAlkylsulfoni
Le, C_Two~ C_FourAlkenylsulfenyl, C_Two~ C_FourArche
Nilsulfinyl, C_Two~ C_FourAlkenylsulfonyl, C
_Two~ C_FourAlkynylsulfenyl, C_Two~ C_FourAlkynyls
Rufinil, C_Two~ C_FourAlkynylsulfonyl, C ₁~ C_Four
Haloalkylsulfenyl, C₁~ C_FourHaloalkylsul
Finil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C_Four
Haloalkenylsulfenyl, C_Two~ C_FourHaloalkenyl
Sulfinyl, C_Two~ C_FourHaloalkenylsulfonyl, C
_Two~ C_FourHaloalkynylsulfenyl, C_Two~ C_FourHaloal
Quinylsulfinyl, C_Two~ C_FourHaloalkynylsulfoni
Le, NO_Two, CN, -NU¹U^Two, Methoki substituted with Ra
Si, C_Two~ C₆Alkoxycarbonyl, C_Two~ C_FourAlkoki
Sialkyl, C_Two~ C_FourAlkylcarbonyl, C_Two~ C_FourC
Loalkylcarbonyl, C_Two~ C_FiveAlkylcarbonyl
Kissi, C_Two~ C_FiveHaloalkylcarbonyloxy, C_Three~
C₇Dialkylaminocarbonyloxy, substituted with Z
Optionally substituted phenyl, Z-substituted phenyl
Nonoxy, benzoyl optionally substituted with Z,
Optionally substituted with pyridyl and Z
1 to 4 positions selected from good pyridyloxy
Or an alkylene group bonded at an adjacent substitution position
Is a 5- to 8-membered ring.

GII: halogen, C₁~ C₆Alkyl, C_Two
~ C_FourAlkenyl, C_Two~ C_FourAlkynyl, C₁~ C_FourHalo
Alkyl, C₁~ C_ThreeC optionally substituted with alkyl
_Three~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C_Two~ C_Four
Alkenyloxy, C_Two~ C_FourAlkynyloxy, C₁~
C_FourHaloalkoxy, C_Two~ C_FourHaloalkenyloxy,
C ₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C_Two~ C_FourAl
Kenylsulfenyl, C_Two~ C_FourAlkenylsulfini
Le, C_Two~ C_FourAlkenylsulfonyl, C_Two~ C_FourAlkini
Rusulfenyl, C_Two~ C_FourAlkynylsulfinyl, C
_Two~ C_FourAlkynylsulfonyl, C₁~ C_FourHaloalkyls
Luphenyl, C₁~ C_FourHaloalkylsulfinyl, C₁
~ C_FourHaloalkylsulfonyl, C_Two~ C_FourHaloalkene
Rusulfenyl, C_Two~ C_FourHaloalkenylsulfini
Le, C_Two~ C_FourHaloalkenylsulfonyl, substituted with Ra
Methoxy, C_Two~ C₆Alkoxycarbonyl, C_Two~
C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloalkyl
Carbonyloxy, phenoxy optionally substituted with Z
In pyridyloxy optionally substituted by Z and Z
1 to 3 substituents selected from

GIII: halogen, C₁~ C₆Alkyl, C₁
~ C_FourHaloalkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, C₁~ C₆Alkoki
Si, C _Two~ C_FourAlkenyloxy, C_Two~ C_FourAlkynyluo
Kissi, C₁~ C_FourHaloalkoxy, C_Two~ C_FourHaloalkene
Luoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourA
Rukylsulfinyl, C₁~ C_FourAlkylsulfonyl, C
_Two~ C_FourAlkenylsulfenyl, C_Two~ C_FourAlkenyls
Rufinil, C_Two~ C_FourAlkenylsulfonyl, C _Two~ C_Four
Alkynylsulfenyl, C_Two~ C_FourAlkynyl sulfy
Nil, C_Two~ C_FourAlkynylsulfonyl, C₁~ C_FourHaloa
Rukylsulfenyl, C₁~ C_FourHaloalkylsulfini
Le, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C_FourHaloa
Lucenylsulfenyl, C_Two~ C_FourHaloalkenyl sulf
Inil, C_Two~ C_FourHaloalkenylsulfonyl, substituted by Ra
Substituted methoxy, C_Two~ C₆Alkoxycarbonyl, C
_Two~ C _FiveAlkylcarbonyloxy, substituted with Z
Phenoxy and pyridi optionally substituted with Z
1 or 2 substituents selected from among ruoxy.

Preferred ranges of R are the following groups. That is, RI: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₃ alkyl substituted with Ra, C ₁ -C ₆ haloalkyl, C
₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy , C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁
-C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl,
C ₂ -C ₄ alkyl Nils Le phenyl, alkynylsulfinyl of _{C 2 ~C 4, C 2 ~C} 4 alkynylsulfonyl, C ₁
-C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C
₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U 2, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, X
1 to 3 substituents selected from phenyl optionally substituted with, pyridyl optionally substituted with X or thienyl optionally substituted with X, or alkylene bonded at an adjacent substituent position 5- to 8-membered ring formed by a group.

RII: halogen, C ₁ -C ₆ alkyl, Ra
C ₁ -C ₃ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₃ optionally C ₃ optionally substituted with alkyl -C ₆ THAT substituted
Cycloalkyl, NO ₂ , CN, —NU ¹ U ² , naphthyl, C _{2 to} C ₄ alkoxycarbonyl, C _{2 to} C ₄ alkoxyalkyl, phenyl optionally substituted by X or optionally substituted by X 1 selected from pyridyl
Or 3 substituents.

RIII: halogen, C₁~ C₆Alkyl, Ra
C substituted with₁~ C_ThreeAlkyl, C ₁~ C₆Haloalk
Le, C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆
Cycloalkyl, NO_Two, CN, -NU¹U^Two, Nahchi
Le, C_Two~ C_FourAlkoxycarbonyl, substituted by X
Optionally substituted phenyl or pyr optionally substituted with X
1 or 2 substituents selected from jyl.

The number of R differs depending on the type of heterocyclic ring substituted by R, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,2 4-thiadiazolyl, 1,2,3
In the case of -oxadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, and preferably 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-
Triazinyl, 1,2,4-triazinyl or 1,
In the case of 2,4-triazinyl, the number of R is from 0 to 2
And preferably 1 or 2. When the heterocyclic ring is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of 0 to 3, preferably 0 to 2, more preferably 1 or 2. It is. When the heterocycle is a pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl group, the number of R is an integer of 0 to 4, preferably an integer of 0 to 3,
More preferably, it is 1 or 2.

Preferred ranges of Y are the following groups. That, YI: halogen, C ₁ -C ₆ alkyl, C ₁ -C
₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄
Haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl Le phenyl, C ₂ ~
C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ ~ C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, C ₂ -C ₄ haloalkylene Nils Le phenyl , C ₂
-C ₄ halo alkynylsulfinyl, C ₂ -C ₄ haloalkynyl ^{_{sulfonyl, NO 2, CN, -NU 1}} U 2, C 2 ~C
1 to 3 substitutions selected from ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -C ₄ haloalkylcarbonyloxy or phenyl optionally substituted by X Base.

YII: halogen, C₁~ C_FourAlkyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourA
Rukylsulfenyl, C₁~ C_FourAlkylsulfinyl,
C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHaloalkyls
Luphenyl, C₁~ C_FourHaloalkylsulfinyl, C₁
~ C_FourHaloalkylsulfonyl, NO_Two, CN, C_Two~ C _Four
Optionally substituted with alkoxycarbonyl or X
1 to 3 substituents selected from phenyl.

The number of Y varies depending on the type of heterocyclic ring substituted by Y, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,2 4-thiadiazolyl, 1,2,3
In the case of thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1
It is. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- In the case of triazinyl or 1,2,4-triazinyl,
The number of Y is an integer of 0 to 2, preferably 1 or 2. When the heterocyclic ring is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of 0 to 3, preferably 0 to 2, more preferably 1 or 2. It is. The heterocycle is pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl,
In the case of isoxazolinyl or thiazolinyl, the number of Y is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 1 or 2.

Preferred ranges of W are the following groups.
You. That is, WI: halogen, C₁~ C₆Alkyl, C₁~ C
_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloa
Lucoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourA
Rukylsulfinyl, C₁~ C_FourAlkylsulfonyl, C
₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C_FourHaloalkylsulfonyl, C
_Two~ C_FourAlkenyloxy, C_Two~ C_FourHaloalkenyloxy
Si, C_Two~ C_FourAlkenylsulfenyl, C_Two~ C_FourArche
Nilsulfinyl, C_Two~ C_FourAlkenylsulfonyl, C
_Two~ C_FourHaloalkenylsulfenyl, C_Two~ C_FourHaloal
Kenylsulfinyl, C_Two~ C_FourHaloalkenylsulfoni
Le, C_Two~ C_FourAlkynyloxy, C_Two~ C_FourAlkynyls
Luphenyl, C_Two~ C_FourAlkynylsulfinyl, C _Two~
C_FourAlkynylsulfonyl, NO_Two, CN, C_Two~ C_FourAl
Coxycarbonyl, C_Two~ C_FourAlkylcarbonyl, C_Two
~ C_FourHaloalkylcarbonyl, C_Two~ C_FourAlkyl cal
Bonyloxy and -NU¹U^TwoOne or more selected from
4 substituents.

WII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ alkenylsulfenyl, C ₂ -C ₄
Alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkynyloxy, C ₂ -C ₄ alkyl Nils Le phenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ ~
1 to 3 substituents selected from C ₄ alkynylsulfonyl, NO ₂ and CN.

WIII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2, CN, to 1 selected from among Two substituents.

Preferred T¹Range is for each group shown below.
You. That is, T¹I: C₁~ C₁₈Alkyl, C_Two~ C₆Arche
Nil, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C
₁~ C_FourAlkyl, C substituted with Ra₁~ C_FourAlkyl,
C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeSubstitute with alkyl
C that may be _Three~ C₆Cycloalkyl, substituted with Ra
Cycloalkyl, C substituted with Ra_Two~ C_FourAl
Kenil, C₁~ C_TenAlkoxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeAlkyl
C which may be replaced_Three~ C₆Cycloalkoxy, benzyl
Luoxy, C_Two~ C_FiveAlkoxycarbonyl, -NU
¹U^TwoPhenyl optionally substituted with Z, substituted with Z
Phenoxy, which may be substituted by Z
May be substituted with phenylthio, naphthyl or Z
Heterocyclic group (however, this heterocyclic group is thienyl, furyl,
Pyrrolyl, oxazolyl, isoxazolyl, thiazoly
, Pyrazolyl, imidazolyl, 1,3,4-oxadi
Azolyl, 1,2,4-oxadiazolyl, 1,3,4
Thiadiazolyl, 1,2,4-thiadiazolyl, 1,
2,4-triazolyl, 1,2,3-thiadiazolyl,
1,2,3-triazolyl, 1,2,3,4-tetrazo
Lil, pyridinyl, pyrimidinyl, pyrazinyl, pyrida
Dinyl, 1,3,5-triazinyl or 1,2,4-
Triazinyl. ).

T ¹ II: C ₁ -C ₁₈ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkyl substituted with Ra, C ₁ ~ C ₃
Optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, cycloalkyl substituted with Ra, C ₂ -C ₄ alkenyl substituted with Ra, C ₁ -C ₁₀ alkoxy, C ₁ -C ₄
Haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₃ -C ₆
Cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted with Z, Z
Or a heterocyclic group optionally substituted with phenoxy, phenylthio, naphthyl or Z (provided that the heterocyclic group is thienyl, furyl, oxazolyl,
Thiazolyl, pyrazolyl or pyridinyl. ).

T ¹ III: C ₁ -C ₁₇ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkyl substituted with phenyl, C ₁ -C ₄ alkyl
₁ -C ₃ alkyl optionally substituted C ₃ -C ₆ cycloalkyl, cycloalkyl substituted with phenyl, C ₂ -C ₄ alkenyl substituted with phenyl, C ₁ -C ₈ alkoxy, C ₁ ~ C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C
₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, which may be substituted with Z phenoxy, phenylthio, naphthyl, optionally substituted optionally substituted with also pyrazolyl or Z in Z pyridinyl It is.

The preferred range of T ² is the following group. That is, T ² I: phenyl, C ₁ -C ₄ alkyl, C _1-
C ₄ alkoxy or C ₁ -C ₄ alkylsulphenyl. Preferred ranges of T ³ are the following groups. That is, T ³ I is phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkylsulfenyl.

Preferred ranges of T ⁴ are the following groups. That is, T ⁴ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ may form a 5- to 7-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bound.

The preferred range of T ⁵ is the following group. That is, T ⁵ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ may form a 5- to 7-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bound.

Preferred ranges of T ⁶ are the following groups. That is, T ⁶ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ may form a 5- to 7-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bound.

Preferred ranges of X are the following groups. That, XI: halogen, C ₁ -C ₄ alkyl, C ₁ -C
₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C
₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄
Haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2,
1 to 3 substituents selected from CN, -NU ¹ U ^{2 and} C _{2 to} C ₅ alkoxycarbonyl.

XII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl Le phenyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, the NO ₂ 1 to 3 substituents selected from among them.

XIII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, 1 to 2 substituents selected from among. The number of X varies depending on the ring substituted by X. When the ring is phenyl, the number of X is an integer of 0 to 5, preferably an integer of 0 to 3. When the ring is pyridyl, the number of X is an integer of 0 to 4, preferably an integer of 0 to 2,
More preferably, it is 0 or 1. In the case of a thienyl group, the number of X is an integer of 0 to 3, preferably 0 or 1.

Preferred ranges of Z are the following groups. That is, ZI: halogen, C ₁ -C ₄ alkyl, C ₁ -C
₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C
₂ -C ₅ alkenyl Le phenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄
Haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2,
1 to 4 substituents selected from CN, -NU ¹ U ^{2 and} C _{2 to} C ₅ alkoxycarbonyl.

ZII: halogen, C₁~ C_FourAlkyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourC
Lower alkoxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C_Two~ C_FiveAlkenylsulfenyl, C_Two~ C_FiveArche
Nilsulfinyl, C_Two~ C_FiveAlkenylsulfonyl, C
₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C _FourIn haloalkylsulfonyl
1 to 4 substituents selected from

The number of Z differs depending on the type of the ring substituted by Z. When the ring substituted by Z is phenyl, the number of Z is 0.
An integer of 0 to 5, preferably an integer of 0 to 4, and more preferably an integer of 0 to 3. When the ring to be substituted by Z is naphthyl, the number of Z is an integer of 0 to 7, preferably 0. When the ring substituted by Z is a heterocyclic group, the number of Z differs depending on the heterocyclic ring, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,
In the case of 2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0. Or 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- Triazinyl or 1,2,4-
In the case of triazinyl, the number of Z is an integer of 0 to 2, preferably 1 or 2. When the heterocyclic ring is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. is there. When the heterocycle is pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of 0 to 4, preferably 0 to 2, more preferably 1 or 2. is there.

Preferred ranges of T ⁷ are the following groups. That is, T ⁷ I: H, phenyl, benzyl or C _1-
It may be C ₄ alkyl or form a 5- or 6-membered ring with the carbon atom to which T ⁷ and T ⁸ are attached. Preferred ranges of T8 are the following groups.

That is, T ⁸ I: phenyl, benzyl or C
₁ -C ₄ alkyl or is, or may form a 5- or 6-membered ring together with the carbon atom to which the T ⁷ and T ⁸ are attached. Preferred ranges of U1 are the following groups. That is,
U ¹ I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅ alkylcarbonyl, or may form a 5- to 7-membered ring with the carbon atom to which U ¹ and U ² are bonded.

Preferred ranges of U ² are the following groups. That is, U ² I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅
It may be alkylcarbonyl or form a 5- to 7-membered ring with the carbon atom to which U ¹ and U ² are attached. Preferred ranges of n are the following groups.

That is, nI: 0, 1 or 2.

Each group in the range of the above-mentioned preferable substituents
Can be combined arbitrarily, and
Preferred ranges of the compounds of the present invention will be described. That is, the preferred location
The range of substituents is QI, AI, BI, L¹I, L^TwoI, L^TwoIV, L
^ThreeI, GI, RI, YI, WI, T¹I, T^TwoI, T^ThreeI, T^FourI, T
^FiveI, T⁶I, XI, ZI, T⁷I, T ⁸I, U¹I, U^TwoI and nI
Certain compounds of the present invention.

Preferred substituent ranges are QI, AI, BII,
GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I,
^{T 6 I, XI, ZI,} T 7 I, T 8 I, U 1 I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QI, AI, BII
I, L ¹ I, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ^{4
I, T 5 I, T 6} I, XI, ZI, T 7 I, T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

Preferred substituent ranges are QI, AI, BIV,
L ² I, L ³ I, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I,
^{T 4 I, T 5 I,} T 6 I, XI, ZI, T 7 I, T 8 I, U 1 I, U 2 I
And nI. The preferred range of substituents is Q
^{I, AI, BIII, L 1} II, GI, RI, YI, WI, T 1 I, T
² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I,
The compound of the present invention, which is U ¹ I, U ² I and nI.

Preferred substituent ranges are QI, AI, BIV,
L ² II, L ³ II, GI, RI, YI, WI, T ¹ I, T ² I, T
³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I, U ¹ I,
The compound of the present invention which is U ² I and nI. A preferred range of the substituent is ^{QI, AI, BIII, L 1} III, GI, RI, YI, WI, T 1
I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I,
T ⁸ I, U ¹ I, a compound of the invention which is U ² I and nI.

Preferred substituent ranges are QI, AI, BIV,
L ² III, L ³ III, GI, RI, YI, WI, T ¹ I, T ² I, T
³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I, U ¹ I,
The compound of the present invention which is U ² I and nI. A preferred range of the substituent is ^{QI, AI, BIV, L 2} IV, GI, RI, YI, WI, T
¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I,
T ⁸ I, U ¹ I, a compound of the invention which is U ² I and nI.

Preferred ranges of the substituents are QII, AII, B
I, L ¹ I, L ² I, L ² IV, L ³ I, GI, RI, YI, WI, T
¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I,
T ⁸ I, U ¹ I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QII, AII, BII, GI, RI, YI, W
I, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI,
The compound of the present invention, which is T ⁷ I, T ⁸ I, U ¹ I, U ² I and nI.

The preferred range of the substituent is QII, AII, BII
I, L ¹ I, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ^{4
I, T 5 I, T 6} I, XI, ZI, T 7 I, T 8 I, U 1 I, a compound of the invention which is U ² I and nI. The preferred substituent range is QI
^{I, AII, BIV, L 2} I, L 3 I, GI, RI, YI, WI, T 1
I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I,
T ⁸ I, U ¹ I, a compound of the invention which is U ² I and nI.

Preferred ranges of the substituents are QII, AII and BI.
V, L^TwoIV, GI, RI, YI, WI, T¹I, T^TwoI, T^ThreeI, T
^FourI, T^FiveI, T⁶I, XI, ZI, T⁷I, T⁸I, U¹I, U^TwoI and
A compound of the present invention which is nI. The preferred substituent range is QI
I, AII, BI, L¹II, L^TwoII, L^TwoIV, L^ThreeII, GII, R
II, YII, WII, T^1II, T^TwoI, T^ThreeI, T^FourI, T^FiveI, T⁶
I, XII, ZII, T ⁷I, T⁸I, U¹I, U^TwoBooks that are I and nI
Invention compound.

Preferred ranges of the substituents are QII, AII and BI.
I, GII, RII, YII, WII, T ¹ II, T ² I, T ³ I, T
⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, T ⁸ I, U ¹ I, U ² I
And nI. The preferred substituent range is QI
^{I, AII, BIII, L 1} II, GII, RII, YII, WII, T 1
II, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T
^The compound of the present invention, which is ⁷ I, T ⁸ I, U ¹ I, U ² I and n.

The preferred substituent ranges are QII, AII, BI
V, L ² II, L ³ II, G II, R II, Y II, W II, T ¹ II, T
² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, T
^The compound of the present invention, which is ⁸ I, U ¹ I, U ² I and nI. A preferred range of the substituent is ^{QII, AII, BIV, L 2} IV, GII, RII,
^{YII, WII, T 1 II,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I,
^{XII, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

The preferred substituent ranges are QII, AII, B
I, L¹II, L^TwoII, L^TwoIV, L^ThreeII, GII, RII, YII,
WII, T^1II, T^TwoI, T^ThreeI, T^FourI, T^FiveI, T⁶I, XII,
ZII, T ⁷I, T⁸I, U¹I, U^TwoA compound of the invention that is I and nI
Stuff. Preferred substituent ranges are QII, AII, BII, GII,
RII, YII, WII, T¹II, T^TwoI, T^ThreeI, T^FourI, T^FiveI,
T⁶I, XII, ZII, T⁷I, T⁸I, U¹I, U^TwoI and nI
The compound of the present invention.

Preferred ranges of the substituents are QII, AII, BII
I, L ¹ II, G II, R II, Y II, W II, T ¹ II, T ² I, T ³
I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, T ⁸ I, U
^The compound of the present invention, which is ¹ I, U ² I and n. A preferred range of the substituent is ^{QII, AII, BIV, L 2} II, L 3 II, GII, RII, Y
II, WII, T ¹ II, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI
^{I, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

Preferred substituents are QII, AII, BI
V, L ² IV, G II, R II, Y II, W II, T ¹ II, T ² I, T ³
I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, T ⁸ I, U
^The compounds of the present invention which are ¹ I, U ² I and nI. A preferred range of the substituent is ^{QII, AII, BI, L 1} III, L 2 III, L 2 IV, L 3 I
II, GIII, RIII, YII, WIII, T 1 III, T 2 I, T
³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹
The compounds of the present invention which are I, U ² I and nI.

The preferred substituent ranges are QII, AII, BI
I, GIII, RIII, YII, WIII, T¹III, T^TwoI, T^ThreeI,
T^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I,
U^TwoThe compound of the present invention, which is I and nI. Preferred range of substituents
Is QII, AII, BIII, L¹III, GIII, RIII, YII,
WIII, T¹III, T^TwoI, T^ThreeI, T^FourI, T^FiveI, T⁶I, XII
I, ZII, T⁷I, T⁸I, U ¹I, U^TwoInvention of I and n
Compound.

Preferred substituent ranges are QIII, AII and BI.
V, L ² III, L ³ III, G III, R III, Y II, W III, T ¹ I
II, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ^{7
I, T 8 I, U 1} I, a compound of the invention which is U ² I and nI. A preferred range of the substituent is ^{QII, AII, BIV, L 2} IV, GIII, R
^{III, YII, WIII, T 1} III, T 2 I, T 3 I, T 4 I, T 5 I,
The compound of the present invention, which is T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I, U ² I and nI.

Preferred substituent ranges are QIII, AIII, B
I, L ¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y
^{II, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I,
^{XIII, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QIII, AIV, BI,
^{L 1 III, L 2 III,} L 2 IV, L 3 III, GIII, RIII, YI
^{I, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, X
^{III, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

The preferred substituent ranges are QIII, AV, B
I, L ¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y
^{II, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I,
^{XIII, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QIV, AIII, BI,
^{L 1 III, L 2 III,} L 2 IV, L 3 III, GIII, RIII, YI
^{I, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, X
^{III, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

Preferred ranges of the substituents are QIV, AIV, B
I, L ¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y
^{II, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I,
^{XIII, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QIV, AV, BI, L
¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y II,
^{WIII, T 1 III, T 2} I, T 3 I, T 4 I, T 5 I, T 6 I, XII
^{I, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

The preferred range of the substituent is QV, AIII, B
I, L ¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y
^{II, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I,
^{XIII, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI. Preferred substituent ranges are QV, AIV, BI, L
¹ III, L ² III, L ² IV, L ³ III, G III, R III, Y II,
^{WIII, T 1 III, T 2} I, T 3 I, T 4 I, T 5 I, T 6 I, XII
^{I, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

The preferred range of substituents is QV, AV, BI,
^{L 1 III, L 2 III,} L 2 IV, L 3 III, GIII, RIII, YI
^{I, WIII, T 1 III,} T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, X
^{III, ZII, T 7 I,} T 8 I, U 1 I, a compound of the invention which is U ² I and nI.

Next, Q, A, B, L ¹ , L ² , L ³ , G,
R, Y, W, X, Z, T 1, T 2, T 3, T 4, T 5, T 6,
Examples of each atom and group in the definition of T ⁷ , T ⁸ , U ¹ or U ² are shown. As the halogen atom in the definition of B, G, R, W, X, Y or Z, a fluorine atom, a chlorine atom,
Examples thereof include a bromine atom and an iodine atom, and preferably include a fluorine atom, a chlorine atom and a bromine atom.

L ¹ , L ² , L ³ , G, R, T ¹ , T ² , T ³ ,
As the alkyl group in the definition of T ⁴ , T ⁵ , T ⁶ , T ⁷ , T ⁸ , U ¹ , U ² , W, X, Y or Z, methyl, ethyl, n -Propyl, isopropyl, n-butyl, isobutyl, tert
-Butyl, sec-butyl, pentyl-1, pentyl-
2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1,2,2-dimethylpropyl-1, hexyl-1,
Hexyl-2, hexyl-3, 1-methylpentyl, 2
-Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, , 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2
-Trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2
-Methylpropyl, n-heptyl, n-octyl, n-
Nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, etc. It is selected in the range of carbon number.

L ¹ , L ² , L ³ , G, R, T ¹ , T ⁴ , T ⁵ ,
The alkenyl group in the definition of T ⁶ , Y or W includes ethenyl as a linear or branched alkenyl group,
1-propenyl, 2-propenyl, 1-butenyl, 2-
Butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2
-Pentenyl, 3-pentenyl, 4-pentenyl, 1-
Methyl-2-butenyl, 2-methyl-2-butenyl, 3
-Methyl-2-butenyl, 1-methyl-3-butenyl,
2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl,
1-hexenyl, 2-hexenyl, 3-hexenyl, 4
-Hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2
-Pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3
-Methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-
4-pentenyl, 1,1-dimethyl-2-butenyl,
1,1-dimethyl-3-butenyl, 1,2-dimethyl-
2-butenyl, 1,2-dimethyl-3-butenyl, 1,
3-dimethyl-2-butenyl, 1,3-dimethyl-3-
Butenyl, 2,3-dimethyl-2-butenyl, 2,3-
Dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-
Butenyl, 1,1,2-trimethyl-2-propenyl,
1-ethyl-1-methyl-2-propenyl and the like, and each is selected from the specified carbon number range.

The alkynyl group in the definition of L ¹ , L ² , L ³ , G, R, Y or W includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl as a linear or branched alkynyl group. 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2
-Pentynyl, 3-pentynyl, 4-pentynyl, 1-
Methyl-2-butynyl, 1-methyl-3-butynyl, 2
-Methyl-3-butynyl, hexynyl, 1-methyl-3
-Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3
-Methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,
2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-
Butynyl and the like, and each is selected from the specified carbon number range.

L ¹ , L ² , L ³ , G, R, T ¹ , W, X, Y
Or a haloalkyl group in the definition of Z includes, as a straight-chain or branched haloalkyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, a fluoroethyl group, a chloroethyl group, a bromoethyl group, and a fluoro-n-
Propyl group, chloro-n-propyl group, difluoromethyl group, chlorodifluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, difluoroethyl group, trifluoroethyl group, trichloroethyl group, chlorodifluoromethyl group, Bromodifluoromethyl group, trifluorochloroethyl group, hexafluoro-
n-propyl group, chlorobutyl group, fluorobutyl group,
Chloro-n-pentyl group, fluoro-n-pentyl group,
Examples thereof include a chloro-n-hexyl group and a fluoro-n-hexyl group, each of which is selected from the specified carbon number range.

[0079] ^{L 1, L 2, L 3} , G, R, T 1, T 4, T 5 or carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms in the definition of T ⁶ 3 to 6 Examples of the cycloalkyl group include a cyclopropyl group, a 1-methylcyclopropyl group, a 2,2,3,3-tetramethylcyclopropyl group, a cyclobutyl group, a 1-ethylcyclobutyl group,
Examples thereof include an n-butylcyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, and a 4-methylcyclohexyl group.

The alkyl group having 1 to 4 carbon atoms and substituted by Ra in the definition of L ¹ , L ² , L ³ , G, R or T ¹ includes benzyl, 2-chlorobenzyl, 3-bromobenzyl Group, 4-chlorobenzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 1-phenylethyl group, 1- (3-chlorophenyl) ethyl group,
-Phenylethyl group, 1-methyl-1-phenylethyl group, 1- (4-chlorophenyl) -1-methylethyl group, 1- (3-chlorophenyl) -1-methylethyl group, 1-phenylpropyl group, 2 -Phenylpropyl group, 3-phenylpropyl group, 1-phenylbutyl group,
2-phenylbutyl group, 3-phenylbutyl group, 4-phenylbutyl group, 1-methyl-1-phenylpropyl group, 1-methyl-2-phenylpropyl group, 1-methyl-3-phenylpropyl group, 2- Examples thereof include a methyl-2-phenylpropyl group, a 2- (4-chlorophenyl) -2-methyl-propyl group, a 2-methyl-2- (3-methylphenyl) propyl group, and the like.

Examples of the cycloalkyl group having 3 to 6 carbon atoms substituted with Ra in the definition of T ¹ include 1-phenylcyclopropyl group, 1- (3-chlorophenyl) cyclopropyl group and 1- (4-chlorophenyl) Cyclopropyl group, 1- (4-bromophenyl) cyclopropyl group, 1
-(4-fluorophenyl) cyclopropyl group, 1-
(4-ethylphenyl) cyclopropyl group, 1- (4-
Propylphenyl) cyclopropyl group, 2-phenylcyclopropyl group, 1-phenylcyclobutyl group, 2-phenylcyclobutyl group, 1-phenylcyclopentyl group, 1- (4-chlorophenyl) cyclopentyl group, 2
-Phenylcyclopentyl group, 3-phenylcyclopentyl group, 1-phenylcyclohexyl group, 1- (3-
(Fluorophenyl) cyclohexyl group, 1- (4-chlorophenyl) cyclohexyl group, 1- (4-tert-butylphenyl) cyclohexyl group, 2-phenylcyclohexyl group, 3-phenylcyclohexyl group, 4-
And a phenylcyclohexyl group.

The cyclopropyl group substituted by Ra and an alkyl group having 1 to 4 carbon atoms in the definition of T ¹ includes 2,2.
2-dimethyl-1-phenylcyclopropyl group, 1-
(4-chlorophenyl) -2,2-dimethylcyclopropyl group, 2,2-dimethyl-3-phenylcyclopropyl group, 3- (3-chlorophenyl) -2,2-dimethylcyclopropyl group, (4-chlorophenyl) −2,2-
Dimethyl-3-phenylcyclopropyl group, (4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl group, 2,2-dimethyl-3- (4-methylphenyl) cyclopropyl group, (4- (Tert-butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl group.

In the definition of T ¹ , the cycloalkyl group having 3 to 4 carbon atoms substituted by Rc and a halogen atom includes:
2,2-dichloro-1-phenylcyclopropyl group,
2,2-dichloro-1- (3-chlorophenyl) cyclopropyl group, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl group, 2,2-dichloro-1-
(4-ethoxyphenyl) cyclopropyl group, 2,2-
Dichloro-1- (4-i-propyloxyphenyl) cyclopropyl group, 2,2-dichloro-1- (4-t-butylphenyl) cyclopropyl group, 2,2-dichloro-
1- (4-methoxyphenyl) -3-phenylcyclopropyl group, 1- (4-ethoxyphenyl) -2,2,
And a 3,3, -tetrafluorobutyl group.

The cyclopropyl group substituted by Rd and an alkyl group having 1 to 4 carbon atoms in the definition of T ¹ includes 2,2
2-dimethyl-3- (2,2-dimethylethenyl) cyclopropyl group, 3- (2,2-dibromoethenyl)-
2,2-dimethylcyclopropyl group, 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropyl group, 3- (2,2-chlorotrifluoroethenyl)-
Examples include a 2,2-dimethylcyclopropyl group.

The cycloalkoxy group having 3 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 3 carbon atoms in the definition of T ¹ includes cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy Group,
And a 1-methylcyclopropoxy group. The alkenyl group having 2 to 4 carbon atoms which is substituted with Ra in the definition of T ^1, 1-phenylethenyl group, 2- phenylethenyl group, 2- (2-chlorophenyl) ethenyl,
2- (3-chlorophenyl) ethenyl group, 2- (4-chlorophenyl) ethenyl group, 2- (4-methylphenyl) ethenyl group, 2- (2,6-difluorophenyl)
Ethenyl group, 2- (2,5-dimethylphenyl) ethenyl group, 1-methyl-2-phenylethenyl group, 2-phenyl-1-propenyl group, 2- (4-bromophenyl)
-1-propenyl group, 2- (2,4,6-trimethylphenyl) -1-propenyl group and the like.

L ² , L ³ , G, R, T ¹ , T ² , T ³ , W,
As the alkoxy group in the definition of X, Y or Z,
A methoxy group as a linear or branched alkoxy group,
Ethoxy, n-propoxy, isopropoxy, n
-Butoxy group, isobutoxy group, sec-butoxy group,
tert-butoxy group, n-pentyloxy group, 1-methylbutyloxy group, 2-methylbutyloxy group, 3-
Methylbutyloxy group, 1,1-dimethylpropoxy group, 1,2-dimethylpropoxy group, 2,2-dimethylpropoxy group, 1-ethylpropyloxy group, n-hexyloxy group, 1-methylpentyloxy group, 2 -Methylpentyloxy group, 3-methylpentyloxy group, 4
-Methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2-dimethylbutyloxy group, 1,3-dimethylbutyloxy group, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group A 3,3-dimethylbutyloxy group, a 1-ethylbutyloxy group, a 2-ethylbutyloxy group, a 1,1,2-trimethylpropyloxy group, a 1,2,2-trimethylpropyloxy group,
1-ethyl-1-methylpropyloxy group and 1-ethyl-2-methylpropyloxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-
A decyloxy group and the like can be mentioned, and each is selected from the specified carbon number range.

C 3 in the definition of G, R or T ¹
Examples of the halocycloalkyl group of Nos. To 6 include a fluorocyclopropyl group, a difluorocyclopropyl group, a chlorocyclopropyl group, a dichlorocyclopropyl group, a 1-methyl-2,2-dichlorocyclopropyl group, a chlorocyclobutyl group, a dichlorocyclo group. Butyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl, tetrafluorocyclobutyl and the like.

In the definition of G, R, T ¹ , W, X, Y or Z, —NU ¹ U ² represents a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, an n-butylamino group, an isobutylamino group. , Sec
-Butylamino group, tert-butylamino group, n-pentylamino group, 1-methylbutylamino group, 2-methylbutylamino group, 3-methylbutylamino group, 1,1
-Dimethylpropylamino group, 1,2-dimethylpropylamino group, 2,2-dimethylpropylamino group, 1-
Ethylpropylamino group, n-hexylamino group, 1-
Methylpentylamino group, 2-methylpentylamino group, 3-methylpentylamino group, 4-methylpentylamino group, 1,1-dimethylbutylamino group, 1,2-
Dimethylbutylamino group, 1,3-dimethylbutylamino group, 2,2-dimethylbutylamino group, 2,3-dimethylbutylamino group, 3,3-dimethylbutylamino group, 1-ethylbutylamino group, 2- Ethylbutylamino group, 1,1,2-trimethylpropylamino group, 1,
2,2-trimethylpropylamino group, 1-ethyl-1
-Methylpropylamino group and 1-ethyl-2-methylpropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, di-n-butylamino group, di-sec-butylamino Group, diisobutylamino group, di-n-pentylamino group, di-n-hexylamino group, methylethylamino group, methylpropylamino group, methylisopropylamino group, methylbutylamino group, methyl-sec-butylamino group, Methyl isobutylamino group, methyl-ter
t-butylamino group, methylpentylamino group, methylhexylamino group, ethylpropylamino group, ethylisopropylamino group, ethylbutylamino group, ethyl-
sec-butylamino group, ethylisobutylamino group,
Ethylpentylamino group, ethylhexylamino group, phenylamino group, benzylamino group, N-methylacetamido group, N-ethylacetamido group, N-phenylacetamido group, N-acetylacetamido group, etc. It is selected in a range of numbers.

The alkoxycarbonyl group having 2 to 5 carbon atoms in the definitions of G, R, T ¹ , W, X, Y and Z includes methoxycarbonyl group, ethoxycarbonyl group, n
-Propoxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, sec-butoxycarbonyl group, iso-butoxycarbonyl group, ter
t-butoxycarbonyl group and the like.

The haloalkoxy group having 1 to 4 carbon atoms in the definition of G, R, T ¹ , W, X, Y and Z includes a straight-chain or branched haloalkoxy group having 1 to 4 carbon atoms, respectively. And fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy Group, chloroethoxy group, bromoethoxy group,
Difluoroethoxy group, trifluoroethoxy group, tetrafluoroethoxy group, pentafluoroethoxy group, trichloroethoxy group, trifluorochloroethoxy group,
Fluoropropoxy group, chloropropoxy group, bromopropoxy group, fluorobutoxy group, chlorobutoxy group,
Fluoro-iso-propoxy group and chloro-iso-
And a propoxy group.

L ¹ , L ² , L ³ , G, R, T ² , T ³ , W,
Examples of the alkylsulfenyl group having 1 to 4 carbon atoms in the definition of X, Y and Z include a methylthio group, an ethylthio group,
n-propylthio group, iso-propylthio group, n-butylthio group, iso-butylthio group, sec-butylthio group and tert-butylthio group. L1, L
2, As the alkylsulfinyl group having 1 to 4 carbon atoms in the definition of L3, G, R, X, W, Y and Z, a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an iso-propylsulfinyl group, n
-Butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl.

The alkylsulfonyl group having 1 to 4 carbon atoms in the definition of L1, L2, L3, G, R, W, X, Y and Z includes methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso -Propylsulfonyl group, n-butylsulfonyl group, iso-butylsulfonyl group, sec-butylsulfonyl group, tert-
And a butylsulfonyl group.

In the definition of L ¹ , L ² , L ³ , G, R, T ¹ or Y, the alkoxyalkyl group having 2 to 4 carbon atoms includes an alkoxy-methyl group having 1 to 3 carbon atoms, an alkoxy-methyl group having 1 to 3 carbon atoms,
2, alkoxy-ethyl group, methoxyethoxymethyl group and methoxypropyl group. G, R, U
^1, the U ^2, Y or W alkylcarbonyl group having 2 to 4 carbon atoms in the definition of an acetyl group, a propionyl group, butanoyl group, iso- butanoyl group.

The haloalkylcarbonyl group having 2 to 6 carbon atoms in the definition of G or W includes a chloroacetyl group, a trifluoroacetyl group, a 3,3,3-trifluoropropionyl group, a pentafluoropropionyl group and the like. Examples of the haloalkylcarbonyloxy group having 2 to 5 carbon atoms in the definition of G, R or Y include a chloroacetyloxy group, a trifluoroacetyloxy group, a 3,3,3
-Trifluoropropionyloxy group, pentafluoropropionyloxy group and the like.

Examples of the dialkylaminocarbonyloxy group having 3 to 7 carbon atoms in the definition of G or Y include a dimethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a diisopropylaminocarbonyloxy group and the like. The naphthyl group in the definition of R, Y, Z and T ¹ includes a 1-naphthyl group and a 2-naphthyl group.

The pyridyl group optionally substituted with Z in the definition of G or T ¹ includes a 2-pyridyl group optionally substituted with Z, a 3-pyridyl group optionally substituted with Z or Z A 4-pyridyl group which may be substituted with, and preferably a 2-pyridyl group which may be substituted with Z.
-A pyridyl group or a 3-pyridyl group optionally substituted with Z, and more preferably a 2-pyridyl group optionally substituted with Z.

The pyridyloxy group optionally substituted with Z in the definition of G or T ¹ includes a 2-pyridyloxy group optionally substituted with Z and a 3-pyridyloxy group optionally substituted with Z. And a 4-pyridyloxy group optionally substituted with a group or. As the pyridyl group optionally substituted with X in the definition of R,
A 2-pyridyl group optionally substituted with X, a 3-pyridyl group optionally substituted with X or a 4-pyridyl group optionally substituted with X, preferably X-substituted A 2-pyridyl group or a 3-pyridyl group optionally substituted with X, more preferably X
Is a 2-pyridyl group which may be substituted.

The pyridyloxy group optionally substituted with X in the definition of R includes a 2-pyridyloxy group optionally substituted with X and a 3-pyridyloxy group optionally substituted with X.
4-optionally substituted with a pyridyloxy group or X
And a pyridyloxy group. Examples of the thienyl group optionally substituted with X in the definition of R include a 2-thienyl group optionally substituted with X and a 3-thienyl group optionally substituted with X.

The thienyl group optionally substituted with Z in the definition of G or Y ¹ includes a 2-thienyl group optionally substituted with Z and a 3-thienyl group optionally substituted with Z.
A thienyl group.

-N = CT ⁷ T ⁸ in the definition of G, R and Y
Represents an alkylideneamino group, a benzylideneamino group, an arylideneamino group or a cycloalkylideneamino group; a methylideneamino group, an ethylideneamino group, a propylideneamino group, an isopropylideneamino group,
Examples thereof include a methyl-2-pentylideneamino group, a cyclopentylideneamino group, and a cyclohexylideneamino group.

In the definition of L ¹ , L ² and L ³ , the number of carbon atoms is 1 to 1.
Examples of the alkylaminosulfonyl group 4 include a methylaminosulfonyl group, an ethylaminosulfonyl group, an n-propylaminosulfonyl group, an isopropylaminosulfonyl group, and an n-butylaminosulfonyl group. Examples of the dialkylaminosulfonyl group having 2 to 8 carbon atoms in the definitions of L ¹ , L ² and L ³ include a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a di-n-propylaminosulfonyl group, a diisopropylaminosulfonyl group and a di-n -Butylaminosulfonyl group and the like.

In the definition of L ¹ , L ² and L ³ , the number of carbon atoms is 2 to 2.
Examples of the alkylaminothiocarbonyl group 5 include a methylaminothiocarbonyl group, an ethylaminothiocarbonyl group, an n-propylaminothiocarbonyl group, an isopropylaminothiocarbonyl group, and an n-butylaminothiocarbonyl group. Examples of the dialkylaminothiocarbonyl group having 3 to 9 carbon atoms in the definition of L ¹ , L ² and L ³ include a dimethylaminothiocarbonyl group, a diethylaminothiocarbonyl group, a di-n-propylaminothiocarbonyl group, a diisopropylaminothiocarbonyl group And a di-n-butylaminothiocarbonyl group.

In the definition of L ¹ , L ² and L ³ , the alkyl group having 1 to 4 carbon atoms and substituted by Rb includes phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromo Phenacyl, 2-methylphenacyl, 3-ethylphenacyl, 4-i-propylphenacyl, 4-t-butylphenacyl and the like.

Examples of the phenylsulfenyl group which may be substituted with a halogen atom or an alkyl group having 1 to 4 carbon atoms in the definition of L ¹ , L ² and L ³ include 2-fluorophenylthio group and 4-fluorophenyl Thio group, 2-chlorophenylthio group, 4-chlorophenylthio group, 4-bromophenylthio group, 2,5-dichlorophenylthio group, pentafluorophenylthio group, 4-methylphenylthio group, 2-methylphenylthio group, 4-t-butylphenylthio group, 2,5-dimethylphenylthio group, 2,4-dimethylphenylthio group, 2,4,6-trimethylphenylthio group, 2,4,6-tri-i-propylphenyl And a thio group.

Examples of the phenylsulfinyl group which may be substituted with a halogen atom or an alkyl group having 1 to 4 carbon atoms in the definition of L ¹ , L ² and L ³ include 2-fluorophenylsulfinyl group and 4-fluorophenylsulfinyl group. Group, 2-chlorophenylsulfinyl, 4-chlorophenylsulfinyl, 4-bromophenylsulfinyl, 2,5-dichlorophenylsulfinyl, pentafluorophenylsulfinyl, 4-methylphenylsulfinyl, 2-methylphenylsulfinyl, 4 -t-butylphenylsulfinyl, 2,5-dimethylphenylsulfinyl, 2,4-dimethylphenylsulfinyl, 2,4,6-trimethylphenylsulfinyl, 2,4,6-tri-i-propylphenylsulfinyl And the like.

The phenylsulfonyl group which may be substituted by a halogen atom or an alkyl group having 1 to 4 carbon atoms in the definition of L ¹ , L ² and L ³ is 2-fluorophenylsulfonyl group, 4-fluorophenylsulfonyl Group, 2-chlorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-bromophenylsulfonyl group, 2,
5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2,4-dimethylphenyl Sulfonyl group, 2,4,6-
And a trimethylphenylsulfonyl group, a 2,4,6-tri-i-propylphenylsulfonyl group and the like.

As the cyanoalkyl group having 2 to 5 carbon atoms in the definition of L ¹ , L ² , L ³ or G, a cyanomethyl group, 2-cyanoethyl group, 3-cyanopropyl group, 1-cyano-1-methylethyl group And the like.

In the definition of L ¹ , L ² and L ³ , the number of carbon atoms is 3 to
Examples of the alkoxycarbonylalkyl group 9 include linear or branched alkoxycarbonylalkyl groups such as methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, i-propoxycarbonylmethyl, and n-butoxycarbonylmethyl. , I-
Butoxycarbonylmethyl group, t-butoxycarbonylmethyl group, n-hexyloxycarbonylmethyl group, n-heptyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 1-n-butoxyethyl group, 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 1-methoxycarbonylpropyl group, 3-ethoxycarbonylpropyl group, 4-methoxycarbonylbutyl group, 6-ethoxycarbonylhexyl group, 1-
Examples include a methoxycarbonyl-1-methylethyl group, a 1-iso-propoxycarbonyl-1-methylethyl group, a 1-ethoxycarbonyl-2-methylpropyl group, and the like.

Examples of the alkali metal in the definition of L ¹ , L ² and L ³ include lithium, sodium and potassium. Examples of the alkaline earth metal in the definition of L ¹ , L ² and L ³ include magnesium, calcium, strontium or barium, and preferably magnesium,
Calcium or barium.

NHT ⁴ T ⁵ in the definition of L ¹ , L ² and L ³
The ammonium group represented by T ^6, ammonium group, monomethyl ammonium group, dimethylammonium group, a trimethylammonium group, diethylammonium group, triethylammonium group, diisopropyl ammonium group, diisopropylethyl ammonium group, a hexyl methyl ammonium group, cyclopropyl A methylammonium group, a cyclohexylmethylammonium group, an allylmethylammonium group, a benzylmethylammonium group or a 4-methylcyclohexylethylammonium group, or two of T ⁴ , T ⁵ and T ⁶ are each bonded Oxygen atom together with nitrogen atom
Heterocyclic five-membered, six-membered, seven-membered or eight-membered ammonium groups which may contain a nitrogen atom or a sulfur atom are exemplified.

The methoxy group substituted by Ra in the definition of G includes benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy,ー t
-Butylbenzyloxy group, 2,6-difluorobenzyloxy group, 2-fluoro-4-chlorobenzyloxy group and the like.

T ⁴ , T ^{5 in} the definition of T ⁴ , T ⁵ or T ⁶
Heterocyclic 5- to 8-membered ammonium groups which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which two of ⁵ and T ⁶ are respectively bonded include pyrrolidine, pyrazolidine, imidazo Lysine, oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine, heptamethyleneimine.

In the definition of G, R, W, X, Y or Z, the haloalkylsulfenyl group has 1 to 4 carbon atoms.
A fluoromethylthio group, a chlorodifluoromethylthio group as a straight-chain or branched-chain haloalkylthio group,
Bromodifluoromethylthio group, trifluoromethylthio group, trichloromethylthio group, 2,2,2, -trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group,
A fluoroethylthio group, a pentafluoroethylthio group and a fluoro-iso-propylthio group.

As the haloalkylsulfinyl group in the definition of G, R, W, X, Y or Z, there are 1 to 4 carbon atoms.
As a linear or branched haloalkylsulfinyl group of fluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, trifluoromethylsulfinyl group, trichloromethylsulfinyl group, 2,2,2, -trifluoro Examples include an ethylsulfinyl group, a 1,1,2,2-tetrafluoroethylsulfinyl group, a fluoroethylsulfinyl group, a pentafluoroethylsulfinyl group, and a fluoro-iso-propylsulfinyl group.

As the haloalkylsulfonyl group in the definition of G, R, W, X, Y or Z, a straight-chain or branched-chain haloalkylsulfonyl group having 1 to 4 carbon atoms is a fluoromethylsulfonyl group, a chlorodifluoromethylsulfonyl group. Group, bromodifluoromethylsulfonyl group, trifluoromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,2, -trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, fluoroethylsulfonyl group And a pentafluoroethylsulfonyl group and a fluoro-iso-propylsulfonyl group.

The haloalkenyl group in the definition of G, R, T1 or W includes a 2-chloroethenyl group as a linear or branched haloalkenyl group having 2 to 4 carbon atoms;
Examples thereof include a 2-bromoethenyl group and a 2,2-dichloroethenyl group.

The alkenyloxy group in the definition of G, R, T ¹ , W or Y includes a straight-chain or branched alkenyloxy group having 2 to 4 carbon atoms such as an allyloxy group, a 2-propenyloxy group or a 2-alkenyloxy group. Butenyloxy group, 2-methyl-2-propenyloxy group and the like. G, R,
As the haloalkenyloxy group in the definition of W or Y, a straight-chain or branched haloalkenyloxy group having 2 to 4 carbon atoms is a 3-chloro-2-propenyloxy group,
-Dichloro-2-propenyloxy group, 4-chloro-2-butenyloxy group, 4,4-dichloro-3-butenyloxy group, 4,4-
And a difluoro-3-butenyloxy group.

The alkenylsulfenyl group in the definition of G, R, W, X, Y or Z includes 2 to 4 carbon atoms.
Allylsulfenyl group as a linear or branched alkenylsulfenyl group, a 2-propenylsulfenyl group,
Examples thereof include a 2-butenylsphenyl group and a 2-methyl-2-propenylsulfenyl group. The alkenylsulfinyl group in the definition of G, R, W, X, Y or Z includes:
Examples of the linear or branched alkenylsulfinyl group having 2 to 4 carbon atoms include an allylsulfinyl group, a 2-propenylsulfinyl group, a 2-butenylsulfinyl group and a 2-methyl-2-propenylsulfinyl group.

The alkenylsulfonyl group in the definition of G, R, W, X, Y or Z includes a straight-chain or branched alkenylsulfonyl group having 2 to 4 carbon atoms, such as an allylsulfonyl group, a 2-propenylsulfonyl group, -Butenylsulfonyl group, 2-methyl-2-propenylsulfonyl group and the like. The haloalkenylsulfenyl group in the definition of G, R, W or Y is a straight-chain or branched haloalkenylsulfenyl group having 2 to 4 carbon atoms.
3-chloro-2-propenylsulfenyl group, 4-chloro-2-butenylsulfenyl group, 3,3-dichloro-2-propenylsulfenyl group, 4,4-dichloro-3-butenylsulfenyl group, 4,4-difluoro-3-butenylsulfenyl group and the like.

The haloalkenylsulfinyl group in the definition of G, R, W or Y includes a straight-chain or branched haloalkenylsulfinyl group having 2 to 4 carbon atoms.
3-chloro-2-propenylsulfinyl group, 3,3-dichloro-
Examples thereof include a 2-propenylsulfinyl group, a 4-chloro-2-butenylsulfinyl group, a 4,4-dichloro-3-butenylsulfinyl group, and a 4,4-difluoro-3-butenylsulfinyl group.

As the haloalkenylsulfonyl group in the definition of G, R, W or Y, a straight-chain or branched haloalkenylsulfonyl group having 2 to 4 carbon atoms is a 3-chloro-2-propenylsulfonyl group, 3,3 -Dichloro-2-propenylsulfonyl group, 4-chloro-2-butenylsulfonyl group, 4,4-dichloro-3-butenylsulfonyl group, 4,4-difluoro-3-butenylsulfonyl group and the like.

C 2 -C 2 in the definition of G, R or W
Examples of the haloalkynyl group 4 include a chloroethynyl group, a bromoethynyl group, an iodoethynyl group, a 3-chloro-1-propynyl group, and a 3-bromo-1-butynyl group.

Examples of the alkynyloxy group having 2 to 4 carbon atoms in the definition of G, R, W or Y include a 2-propynyloxy group, a 2-butynyloxy group and a 1-methyl-2-propynyloxy group. Examples of the haloalkynyloxy group having 2 to 4 carbon atoms in the definition of G, R, W or Y include a 3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy group, and a 3-iodo-2-propynyl. Oxy groups and the like.

The alkynylsulfenyl group having 2 to 6 carbon atoms in the definition of G, R, W or Y includes 2-propynylsulfenyl, 2-butynylsulfenyl, 1-methyl-2-propynylsulfenyl And the like.
Examples of the alkynylsulfinyl group having 2 to 6 carbon atoms in the definition of G, R, W or Y include a 2-propynylsulfinyl group, a 2-butynylsulfinyl group and a 1-methyl-2-propynylsulfinyl group.

The alkynylsulfonyl group having 2 to 6 carbon atoms in the definition of G, R, W or Y includes 2-propynylsulfonyl group, 2-butynylsulfonyl group, 1-methyl-2
-Propynylsulfonyl group and the like. G, R, W
Or the haloalkynylsulfenyl group having 2 to 6 carbon atoms in the definition of Y includes 3-chloro-2-propynylsulfenyl group, 3-bromo-2-propynylsulfenyl group, 3-iodo-2-propynylsulfur group And a phenyl group.

As the haloalkynylsulfinyl group having 2 to 6 carbon atoms in the definition of G, R, W or Y,
Chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-iodo-2-propynylsulfinyl and the like. Examples of the haloalkynylsulfonyl group having 2 to 6 carbon atoms in the definition of G, R, W or Y include a 3-chloro-2-propynylsulfonyl group and a 3-bromo-
Examples thereof include a 2-propynylsulfonyl group and a 3-iodo-2-propynylsulfonyl group.

The alkylcarbonyloxy group having 2 to 4 carbon atoms in the definition of G, R, W or Y includes an acetoxy group, a propanoyloxy group, a butanoyloxy group,
An isopropylcarbonyloxy group and the like can be mentioned. The benzoyl group optionally substituted by X in the definition of G includes a benzoyl group, a 2-chlorobenzoyl group,
Chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl, 3,4-dichlorobenzoyl, etc. Is raised.

Examples of the case where L ² and L ^{3 in} the definition of L ² and L ³ together with these bonded nitrogen atoms form a 5- to 8-membered ring having one or more hetero atoms include pyrrole and imidazole. , Pyrazole, triazole, tetrazole, pyrrolidine, piperidine, piperazine, morpholine and the like.

The compounds of the present invention can be used in so-called agricultural pests that damage agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that have various adverse effects on human living environments such as houses, and warehouses. The so-called stored pests that injure stored grains and the like, and any pests such as mites, nematodes, molluscs, and crustaceans that occur and injure in similar situations can be effectively controlled at low concentrations.

Insects which can be controlled using the compounds of the present invention;
Specific examples of mites, nematodes, molluscs, and crustaceans include the following, but are not limited thereto. P. serrata, P. serrata, P. serrata, P. serrata, P. serrata, P. japonicus, P. serrata, P. japonicus, P. serrata, P. serrata, P. serrata, P. s. Bowler, fall army worm,
Lepidopteran pests such as codling moths and white-winged starlings, leafhoppers, leafhoppers, brown peach aphids, cotton aphids, cotton aphids, onyx whitefly, tobacco whitefly, pear lice, tsujigumbai, red-spotted beetles, beetles, beetles, etc. Winged pests,
Scarlet beetle, Douganebuuibu, rice water weevil, arimodoki weevil, turtle leaf beetle, cypress flea beetle, colorado beetle, sesame beetle, pine beetle beetle, corn root worm, cocoon elephant, granary weevil, moss Hessian flies, sea flies, medfly, houseflies, flies,
Sheep flies, flies, bullflies, sheep flies, tsetse flies, mosquitoes, Aedes aegypti,
Diptera pests such as Anopheles, Hymenoptera, Pinus sylvestris and Hymenoptera such as Hymenoptera, Thrips palmi, Thrips palmi, Thrips palmi,
Pterodactyl pests such as Thrips thrips and Thrips palmi, Thrips palmi, Thrips japonicus, German cockroaches, etc. Eye pests, cat flea, human flea, isopteryx pests such as mosquito flea, chicken lice, lice lice such as lice, lice, lice such as lice, lice, lice, lice, mites, spider mites, and red spider mites. Spider mites such as red mites, red rust mite, red rust mite, tulip rust mite, red ticks, etc .; , Acarina mites, Acarina mites such as Robin's mite, Dermatophagoid mites such as Honey beetle mites, Dermatophagoid mites such as Oxodid tick, Haemaphysalis longicornis, Dermatophagoides mite such as Dermatophagoid mite, Sweet potato nematode, Kitako Neko nematode, Kitanegusa nematode nematode, Dermatophagoidea nigra Nematodes such as nematodes and pine wood nematodes,
Examples include mollusks such as scallops, slugs, scuttles, and mussels, and crustaceans such as locust beetles.

That is, the compounds of the present invention can effectively control pests and plant diseases such as Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Mite and Lice at low concentrations. it can. On the other hand, the compounds of the present invention include extremely useful compounds having almost no adverse effects on mammals, fish, crustaceans and beneficial insects. The compound of the present invention can be synthesized by the following method.

When B of the compound (1) of the present invention is a halogen atom, the synthesis method is as follows: Polymer Burtin 28 vol. 381
Page 1992 @ Polymer Bulleti
n, 28, 381 (1992)}.
The synthesis method when B of the compound (1) of the present invention is S (O) n is described in Journal Heterocyclic Chemistry.
Vol. 27, No. 3, page 647 1990 {J. Hete
rocycl. Chem. , 27 (3), 647 (19
90)｝ and Chemische Berichte 100 Volume 141
3 page 1967 @Chem. Ber. , 10
0,1413 (1967)}.

When B of the compound (1) of the present invention is NL ² L ³ , the compound was synthesized by the following method. When L ² and L ³ are hydrogen atoms, Chemical and Pharmaceutical Calburtin, Vol. 33, No. 3, page 975, 1985 {Chem. Pharm. Bull. , 33 (3), 9
75 (1985). When L ² and L ³ are other than a hydrogen atom, see Journal Heterocyclic Chemistry, Vol. 27, No. 3, page 647 (1990)
Year @J. Heterocycl. Chem. , 27
(3), 647 (1990)} and Polymer Bullin 28, 381, 1992 {Polymer
Bulletin, 28, 381 (1992)}.

When B of the compound (1) of the present invention is S (O) n, it can also be synthesized by the following method.

[0135]

Embedded image

Q and A in (Scheme 1) have the same meanings as described above, and B 'is a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom) or trifluoromethanesulfonyloxy, C1-C4 alkylmethanesulfonyl. Represents oxy, benzenesulfonyloxy, toluenesulfonyloxy and the like. (Scheme 1) is a synthesis method in which B of the compound (1) of the present invention is S (O) n. That is,
(Scheme 1) shows that (1a) which is a part of the compound (1) of the present invention is synthesized by reacting (3) with thioalcoholate (4). Further, by reacting (1a) with a suitable oxidizing agent (eg, aqueous hydrogen peroxide, m-chloroperbenzoic acid, etc.), the target compound (1a ′) is obtained.
Can be converted to

When B of the compound (1) of the present invention is NL ² L ³ , it can also be synthesized by the following method.

[0138]

Embedded image

Q and A in (Scheme 2) have the same meanings as described above, and L ′ represents L ² or L ³ . (Scheme 2)
Is a synthesis method when B of the compound (1) of the present invention is NL ² L ³ . That is, (Scheme 2) is a synthesis method in which one of L ^{2 and} L ³ is a hydrogen atom, and amide compound (5) is converted to imidoyl halide (6) with an appropriate halogenating agent and reacted with (7). This is a method for synthesizing (1b) which is a part of the target compound (1).

In some cases, it is preferable to use a base in the method described above. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide and potassium t-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. ,
Examples thereof include organic bases such as triethylamine, pyridine and DBU, organic lithium compounds such as butyllithium, lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide, and sodium hydride.

The above-mentioned reaction can be carried out in a solvent inert to the reaction. Examples of the solvent include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether and tetrahydrofuran. , 1,4-dioxane, 1,2-dimethoxyethane,
Ethers such as 1,2-diethoxyethane, halogenated hydrocarbons such as methylene chloride, chloroform, and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, and a mixed solvent thereof, and the like Is mentioned. In some cases, a mixed solvent of these solvents and water can also be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. The reaction temperature ranges from -70 ° C to 2
The temperature can be set at an arbitrary temperature of 00 ° C., and preferably from 0 ° C. to 150 ° C. or from −70 ° C. to the boiling point of the solvent when a solvent is used. The base is 0.05 of the reaction substrate.
To 10 equivalents, preferably 0.05 to 3 equivalents.

The compound of the present invention can be obtained from the reaction solution by a conventional method. However, when it is necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization and column chromatography. Can be. The compounds having an asymmetric carbon among the compounds included in the present invention include optically active compounds (+) and (−).

Examples of the compounds included in the present invention are shown in Table 1. The abbreviations in the table have the following meanings. M
e: methyl group, Et: ethyl group, Pr: propyl group, B
u: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, No
n: nonyl group, Dec: decyl group, Ph: phenyl group,
n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo, [Table 1]

[0144]

Embedded image

[0145]

Embedded image

[0146]

Embedded image

[0147]

Embedded image

[0148]

Embedded image

[0149]

Embedded image

[0150]

Embedded image

[0151]

Embedded image

[0152]

[Table 1] {QABBR'Y '} ───────────────────────────────── Q1 A16 Cl Br Me Q2 A17 F CO ₂ CF ₃ Me Q3 A18 Br Ph Me Q4 A19 I Ph Me Q7 A8 SH Ph Cl Q9 A8 SMe 2-pyridyl Cl Q9 A8 SMe 2,6-F ₂ -PhCl Q46 A46 SMe t-Bu Me Q8 A46 SMe sec-Bu Me Q6 A20 SCH ₂ CH = CH ₂ CH = CH ₂ Me Q7 A21 SCH ₂ CH≡CH ₂ 2-Naphthyl Ph Q8 A22 Sc-Pr CH ₂ CO ₂ Et Ph Q9 A23 SCF ₃ OCO ₂ Me Ph Q10 A24 SCH ₂ OCH ₃ C≡CCl Ph Q11 A25 SCH ₂ SCH ₃ Ph Ph Q12 A26 SCH ₂ OCH ₂ OCH ₃ SCH ₂ C≡CCl Me Q13 A27 SPh Ph Me Q14 A28 SCH ₂ Pht-Bu Me Q15 A29 SCH ₂ C (O) Ph Ph Me Q16 A30 B1 Ph Me Q17 A31 SSMe Ph Ph 18 A32 SS (O) Me Ph Ph Q19 A33 SSO 2 Me Ph CH 2 CH = CF 2 ───────────────────────────── ───────

[0153]

[Table 2] {QABBR'Y '} ───────────────────────────────── Q20 A34 SSPh CH ₂ Ph H Q21 A35 SS (O) Ph OC (O ) CF ₃ H Q22 A36 SSO ₂ Ph Ph H Q23 A37 SSO ₂ CF ₃ Ph H Q24 A38 SSO ₂ NHMe Ph H Q25 A39 SSO ₂ NMe ₂ Ph H Q37 A40 SSO ₂ NHPh HH Q38 A41 SC (S) NHMe HH Q40 A42 SC (S) NMe ₂ HH Q38 A41 SC (O) NHMe HH Q40 A42 SC (O) NMe ₂ HH Q41 A43 SCH ₂ CN HH Q8 A45 SCH ₂ C (O) OMe Ph H Q21 A46 SC (O) Ph OCH2C≡ CH Me Q33 A1 SC (O) Me Ph F Q33 A2 SC (O) CF ₃ PhCl Q42 A3 SC (O) -c-PrHCl Q7 A8 SC (O) -t-Bu PhCl Q43 A4 SC (S ) Me H CF ₃ Q44 A5 SP (O) (OMe) ₂ HMe Q45 A6 SP (S) (OMe) ₂ HMe Q47 A7 SNa H CF ₃ Q9 A8 S (O) Me 2,6-F ₂ -Ph Cl ──────────────────────────────── ────

[0154]

[Table 3] {QABBR'Y '} ───────────────────────────────── Q6 A20 S (O) CH ₂ CH = CH ₂ Ph Ph Q7 A21 S (O) CH ₂ CH≡CH ₂ Ph Ph Q8 A22 S (O) -c-Pr Ph Ph Q9 A23 S (O) CF ₃ Ph Ph Q10 A24 S (O) CH ₂ OCH ₃ Ph Ph Q11 A25 S (O ) CH ₂ SCH ₃ Ph Ph Q12 A26 S (O) CH ₂ OCH ₂ OCH ₃ Ph Ph Q13 A27 S (O) Ph Ph Ph Q14 A28 S (O) CH ₂ Ph Ph Ph Q46 A8 SO ₂ Me OCH ₂ OMe Cl Q6 A20 SO ₂ CH ₂ CH = CH ₂ C≡CCl Ph Q7 A21 SO ₂ CH ₂ CH≡CH ₂ OCH ₂ C≡CCl Ph Q9 A23 SO ₂ CF ₃ C (O) Me Ph Q10 A24 SO ₂ CH ₂ OCH ₃ Ph Ph Q11 A25 SO ₂ CH ₂ SCH ₃ Ph Ph Q12 A26 SO ₂ CH ₂ OCH ₂ OCH ₃ Ph Me Q13 A27 SO ₂ Ph Ph Me Q14 A28 SO ₂ CH ₂ Ph Ph Me Q8 A8 SNa CH = CH ₂ CF ₂ Br Q8 A9 SNHEt ₃ C≡CH OMe Q46 A53 SC (O) NHPh OCH ₂ C≡CCl Me Q8 A44 NH ₂ t-Bu H Q8 A44 NH ₂ t-Bu Cl ─────────────────────────────

[0155]

[Table 4] {QABBR'Y '} ───────────────────────────────── Q7 A8 NHMe Ph Cl Q1 A44 NHOMe Cl OMe Q2 A48 NHCH ₂ CH = CH _{2 CO 2 Et OCH 2 CH =} CH 2 Q3 A49 NHCH 2 C≡CH Ph OCH 2 C≡CH Q4 A44 NH-c-Pr Ph OCF 3 Q5 A48 NHCF 3 Ph OCH 2 CH = CF 2 Q6 A44 NHCH 2 OCH 3 CH ₂ Ph OCH ₂ C≡CCl Q7 A44 NHCH ₂ SCH ₃ c-Pr Me Q8 A48 NHCH ₂ OCH ₂ OCH ₃ CH2OMe SCF ₃ Q9 A48 NHPh 2-thienyl S (O) CF ₃ Q10 A48 NHCH ₂ Ph 2-pyridyl SO ₂ CF ₃ Q11 A49 NHCH ₂ C (O) Ph NO ₂ SCH ₂ CH = CCl ₂ Q12 A49 4-morpholino SMe S (O) CH ₂ CH = CCl ₂ Q13 A49 1-Piperidino Ph S0 ₂ CH ₂ CH = CCl ₂ Q14 A44 NHSO ₂ Me-Bu SCH ₂ C≡CCl Q15 A44 NHSO ₂ Ph Ph S (O) CH ₂ C≡CCl Q16 A44 NHSO ₂ CF ₃ t-Bu SO ₂ CH ₂ C≡CCl Q17 A48 NHSO ₂ NHMe Ph OH Q18 A48 NHSO ₂ NMe ₂ Ph CH ₂ OMe Q19 A49 NHSO ₂ NHPh Ph OC (O) Me Q19 A49 NHC (O) NHMe Ph CONMe ₂ Q21 A49 NHC (O) NMe ₂ CF ₃ 2-thienyl Q19 A49 NHC (S) NHMe Ph CONMe ₂ ────────────────── ──────────────────

[0156]

[Table 5] {QABBR'Y '} ───────────────────────────────── Q21 A49 NHC (S) NMe ₂ CF ₃ 2-pyridyl Q22 A50 NHCH ₂ CN t-Bu SMe Q23 A50 NHCH ₂ C (O) OMe Ph S (O) Me Q24 A50 NHC (O) Me Ph SO ₂ Me Q25 A50 NHC (O) CF ₃ Ph SCH ₂ CH = CH ₂ Q26 A50 NHC ( O) -c-Pr Ph S (O) CH ₂ CH = CH ₂ Q27 A50 NHC (O) Ph Ph SO ₂ CH ₂ CH = CH ₂ Q28 A50 NHP (O) (OMe) ₂ Ph SCH ₂ C≡CH Q29 A50 NHP (S) (OMe) ₂ Ph S (O) CH ₂ C≡CH Q30 A50 NHC (O) CH ₂ CH = CH ₂ Ph SO ₂ CH ₂ C≡CH Q8 A44 NHC (O) CH2C (O) Me t-Bu H Q8 A44 NHC ( O) CH2C (O) Me t-Bu Cl Q7 A8 NMe 2 2-F - Ph Cl Q8 A7 NMe 2 t-Bu Me Q8 A8 NMe 2 2- morpholino Cl Q8 A8 NMe ₂ t -Bu Cl Q9 A8 NMe ₂ 2,6-F _2- Ph Cl Q46 A8 NMe ₂ t-Bu Cl Q8 A7 N (OMe) Me t-Bu Me Q8 A7 N (OMe) ₂ t-Bu Me Q46 A8 N (CH ₂ CH = CH ₂ ) ₂ t-Bu Cl Q31 A51 NMe (c -Pr) Ph CN Q32 A51 NMe (CF ₃ ) Ph NMe ₂ ─────────────────────────────────── ─

[0157]

[Table 6] {QABBR'Y '} ───────────────────────────────── Q33 A9 NMe (CH ₂ OMe) Ph NO ₂ Q34 A52 NMe (CH ₂ OMe) SMe) Ph CO ₂ Me Q35 A1 NEt (CH ₂ OCH ₂ OMe) C (Me) = CCl ₂ Cl Q36 A2 NMePh H Cl Q39 A3 NPh ₂ HCl Q46 A4 N (CH ₂ Ph) ₂ SCH ₂ C≡CH Me Q46 A5 NMe (CH ₂ Ph) S (O) CH ₂ C≡CH Me Q46 A6 NMe {CH ₂ C (O) Ph} S0 ₂ CH ₂ C≡CH Me Q46 A7 NMe (SO ₂ Me) SCH ₂ C = _{CF 2 CF 3 Q46 A8 N (} i-Pr) (SO 2 CF 3) S (O) CH 2 C = CF 2 CF 3 Q46 A10 NMe (SO 2 NHMe) S0 2 CH 2 C = CF 2 CF 3 Q12 A11 NMe (SO ₂ Ph) SO ₂ Me Me Q12 A12 NMe {C (O) NHMe} S (O) Me Me Q21 A13 NMe {C (O) NMe ₂ } OMe Me Q12 A12 NMe {C (S) NHMe} S (O) Me Me Q21 A13 NMe {C (S) NMe ₂ } OMe Me Q21 A14 N (CH ₂ CN) ₂ OPh Me Q21 A15 NMe {CH ₂ C (O) OMe} OCH ₂ CH = CH ₂ Me Q46 A47 NMeC (O) Me OCF ₃ i-Pr Q46 A47 NMeC (O) CF ₃ OCH ₂ CH = CF ₂ Et Q46 A7 NMeC (O) -c-Pr S (O) CH ₂ CH = CH ₂ OMe Q46 A8 NMeC (O) Ph SO ₂ CH ₂ CH = CH ₂ i-Pr Q46 A9 NMe (SO ₂ NHPh) SO ₂ CF ₃ OCF ₃ ────────────────────────────────────

[0158]

[Table 7] {QABBR'Y '} ───────────────────────────────── Q46 A4 NMe (SO ₂ NMe ₂ ) SCF ₃ CF ₃ Q7 A8 1- pyrazolyl _{2-F - Ph Cl Q8 A7} 1- imidazolyl t-Bu Me Q8 A8 1- triazolyl 2- morpholino Cl ───────────────────────── ───────────

When the compound of the present invention is applied as a pesticidal agent, it is usually mixed with an appropriate solid carrier or liquid carrier, and if necessary, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent, Binders, anti-caking agents, disintegrants and decomposition inhibitors are added, and liquids, emulsions, wettable powders, aqueous solvents,
It can be practically used in any form of formulation such as water dispersible granules, aqueous solvents for granules, suspensions, emulsions, suspoemulsions, microemulsions, powders, granules and gels. Further, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package.

Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. And the like, synthetic silicic acid and synthetic silicate. As liquid carriers, for example, alcohols such as ethylene glycol, propylene glycol and isopropanol,
Aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; Vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil and water.

These solid and liquid carriers may be used alone or in combination of two or more. As a surfactant,
Nonionic properties such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester Surfactant, alkyl sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of naphthalene sulfonic acid formalin condensate, alkyl naphthalene sulfonic acid formalin Salts of condensates, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styryl phenylate Anionic surfactants such as sulfuric acid and phosphates, polycarboxylates and polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkylquaternary ammonium salts, and amphoteric surfactants such as amino acid type and betaine type Is mentioned.

The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more. When the compound of the present invention is used as a pesticide, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, plant growth regulators and the like may be used as needed during formulation or spraying. You may mix and apply with a power agent, a fertilizer, a soil conditioner, etc.

In particular, by applying a mixture with other agricultural chemicals or plant hormones, it is expected that the cost can be reduced by reducing the amount of the applied medicine, the insecticidal spectrum can be expanded by the synergistic action of the mixed medicine, and a higher pest control effect can be expected. On this occasion,
A combination with a plurality of known pesticides is also possible at the same time. Examples of the kind of pesticide to be used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm
Chemicals Handbook), 1994, and the like.

The applied amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but is generally 0.000 per hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate. Next, a formulation example of a preparation when the compound of the present invention is used is specifically shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, an anti-caking agent and a decomposition inhibitor. .

[Emulsion] 0.1 to 30 parts of the compound of the present invention 45 to 95 parts of a liquid carrier Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, a spreading agent and a decomposition inhibitor.

[Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, an antifreezing agent and a thickener.

[Water dispersible granule] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor.

[Solution] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, an antifreezing agent and a spreading agent.

[Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor.

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, a drift inhibitor, a decomposition inhibitor and the like.

[0172]

EXAMPLES The synthesis examples, preparation examples, and test examples of the compound of the present invention are specifically described below as examples, but the present invention is not limited to these examples.

Synthesis Example 1 Synthesis of 2- (4-tert-butylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-chloroacrylonitrile (Compound No. 1) 2- (4-tert-butylphenyl) -3- (1,
3-dimethyl-5-chloropyrazol-4-yl) -3
1.9 g of -hydroxyacrylonitrile was dissolved in 1,2-dichloroethane, 1.44 g of phosphorus pentachloride was added, and the mixture was stirred under reflux for 2 hours. After cooling, the solvent was distilled off under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate = 3/1) to obtain 1.70 g of the desired compound. ^{1 H-NMR (CDCl3, δppm} ) 1.28 (9H, s), 1.85 (3H, s), 3.77 (3H, s), 7.15-7.18 (2H, m),
7.26-7.29 (2H, m)

[Synthesis Example 2] 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-
Methylsulfenyl acrylonitrile (compound NO.
Synthesis of 2) 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-trifluoromethanesulfonyloxyacrylonitrile 1.0 g was dissolved in 15 ml of tetrahydrofuran, 0.18 g of sodium thiomethylate was added under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water.
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate = 2/1) to give the desired compound 0.4
0 g was obtained (E / Z mixture major / minor = 3/1). ^{1 H-NMR (CDCl3, δppm} ) major: 2.06 (3H, s), 3.92 (3H, s), 6.28-6.83 (1H, m), 6.98-
7.33 (3H, m), 7.96 (1H, d) minor: 2.24 (3H, s), 3.80 (3H, s), 5.99-6.15 (1H, m), 6.50-
7.33 (3H, m), 7.58 (1H, d) [Synthesis Example 3] 2- {3- (2-pyridyl) pyrazole-
Synthesis of 1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-methylsulfenylacrylonitrile (Compound No. 3) The above compound was synthesized in the same manner as in Synthesis Example 2. did. ¹ H-NMR (CDCl3, δ ppm) 2.06 (3H, s), 3.91 (3H, s), 7.16-7.33 (2H, m), 7.63-8.21 (3
H, m), 8.64-8.71 (1H, m)

[Synthesis Example 4] 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-
Methylsulfinyl acrylonitrile (compound NO.
Synthesis of 4) 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-methylsulphenylacrylonitrile 0 0.4 g in 5 ml of dichloromethane,
Under ice-cooling, 0.19 g of m-chlorobenzoic acid was added, and the mixture was stirred for 1 hour. The reaction solution was poured into ice water, extracted with chloroform, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by preparative high performance liquid chromatography (acetonitrile / water = 4/1) to obtain 0.10 g of the desired compound (E-Z mixture major). / minor = 3/1). ^{1 H-NMR (CDCl3, δppm} ) major: 3.01 (3H, s), 3.91 (3H, s), 7.00-7.07 (3H, m), 7.37-
7.41 (1H, m), 8.08-8.09 (1H, m) minor: 3.06 (3H, s), 3.93 (3H, s), 7.00-7.07 (3H, m), 7.37-
7.41 (1H, m), 8.08-8.09 (1H, m)

Synthesis Example 5 Synthesis of 2- (2-s-butylthiazol-4-yl) -3- (3,5-dimethylpyrazol-1-yl) -3-methylthioacrylonitrile (Compound No. 5) 2.1 g of 2-s-butyl-4-cyanomethylthiazole
Is dissolved in 40 ml of tetrahydrofuran, and 55% at room temperature.
0.51 g of sodium hydride was added and stirred for 30 minutes.
To this was added 1.45 g of 3,5-dimethyl-1-methylthiocarbonylpyrazole, and the mixture was stirred at room temperature for 1 hour, and further stirred under reflux for 2 hours. After cooling, tetrahydrofuran was distilled off under reduced pressure, 80 ml of water was added, and 1.5 g of dimethyl sulfate was added.
Was added dropwise and stirred for 2 hours. After ethyl acetate was added to the reaction solution and the layers were separated, the ethyl acetate layer was washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate = 5/1) to give 2- (2-s-butylthiazole-4-). 1.20 g of (yl) -3- (3,5-dimethylpyrazol-1-yl) -3-methylthioacrylonitrile were obtained (E-Z mixture). ¹ H-NMR (CDCl3, δ ppm) 0.93 (1.5H, t), 0.98 (1.5H, t), 1.26 (1.5H, d), 1.43 (1.5H,
d), 1.50-1.95 (3.5H, m) 2.00 (1.5H, s), 2.05 (1.5H, s), 2.28 (1.5H, s), 2.30 (1.5H,
s), 2.35 (1.5H, s), 2.97 (0.5H,), 3.17 (0.5H,), 5.97 (0.5H
H, s), 6.02 (0.5H, s), 6.56 (0.5H, s), 7.55 (0.5H, s)

[Synthesis Example 6] 2- (4-tert-butylphenyl) -3- (3,5-dimethylpyrazole-1
-Yl) -3-methylthioacrylonitrile (compound N
O. Synthesis of 6) The above compound was synthesized in the same manner as in Synthesis Example 5 (E
-Z mixture major / minor = 3/2). ¹ H-NMR (CDCl3, δppm) major: 1.25 (9H, s), 1.86 (3H, s), 2.03 (3H, s), 2.31 (3H, s),
5.87 (1H, s), 6.89-6.91 (2H, m), 7.22-7.24 (2H, m) minor: 1.35 (9H, s), 1.80 (3H, s), 2.31 (3H, s), 2.39 (3H , s),
6.03 (1H, s), 7.47-7.49 (2H, m), 7.58-7.60 (2H, m)

Synthesis Example 7 Synthesis of 2- {2-tert-butylthiazol-4-yl} -3-phenyl-3-aminoacrylonitrile (Compound No. 7) 1) n-Butyllithium (1.54 mol) / L) Cool the hexane solution to -70 ° C and add diisopropylamine 0.
83 g was added dropwise and stirred for 10 minutes. To this was added 2-tert-butyl riazole-4-cyanomethylthiazole.
Dissolve 35 g in 10 ml of tetrahydrofuran and add dropwise,
Subsequently, 6-methyl-2-phenyl-4H-1,3-oxazin-4-one was dissolved in 10 ml of tetrahydrofuran and added dropwise. The mixture was stirred at -70 ° C for 2 hours, adjusted to pH 4 by adding a 10% aqueous hydrochloric acid solution, and tetrahydrofuran was distilled off under reduced pressure. Chloroform was added to the residue and the mixture was separated, and the chloroform layer was washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, n-hexane / ethyl acetate = 2/2).
Purification in 1) gave 1.20 g of 2- {2-tert-butylthiazol-4-yl} -3-phenyl-3-acetamidoacrylonitrile. ^{1 H-NMR (CDCl3, δppm} ) 1.45 (9H, s), 2.25 (3H, s), 3.70 (2H, s), 7.25 (1H, s), 7.42-
7.55 (5H, m), 12.9 (1H, b)

2) After heating 0.80 g of 2- {2-tert-butylthiazol-4-yl} -3-phenyl-3-acetamidoacrylonitrile at 180 ° C. for 3 hours, column chromatography (silica gel, n- Hexane / ethyl acetate = 3/1) to give 2- {2-
Shaributylthiazol-4-yl} -3-phenyl-
1.20 g of 3-aminoacrylonitrile were obtained. ^{1 H-NMR (CDCl3, δppm} ) 1.47 (9H, s), 4.90 (1H, b), 7.13 (1H, s), 7.47-7.48 (3H, m),
7.63-7.66 (2H, m), 9.35 (1H, b)

[Synthesis Example 8] 2- {2-tert-butylthiazol-4-yl} -3- (2-chlorophenyl)
Synthesis of -3-aminoacrylonitrile (Compound No. 8) The above compound was synthesized in the same manner as in Synthesis Example 7. 1) 2- {2- motor - rice butyl-4-yl} -3- (2-chlorophenyl) -3-acetamide acrylonitrile ^{1 1 H-NMR (CDCl3,} δppm) 1.16 (9H, s), 2.31 (3H , s), 3.57 (2H, s) 6.88 (1H, s), 7.21-7.
48 (4H, m), 9.85 (1H, b) 2) 2- {2-tert-butylthiazol-4-yl} -3- (2-chlorophenyl) -3-aminoacrylonitrile ¹ H-NMR (CDCl3, δppm) 1.48 (9H, s), 4.80 (1H, b), 7.12 (1H, s), 7.37-7.52 (4H, m),
9.30 (1H, b)

Synthesis Example 9 2- {4-phenylthiazol-2-yl} -3- (3,5-dichloro-1-methyl-pyrazol-4-yl) -3-methylaminoacrylonitrile (compound NO. Synthesis of 9) 1.0 g of 1-methyl-3,5-dichloropyrazole-4-carboxymethylamide was dissolved in 15 ml of toluene, 1.2 g of phosphorus pentachloride was added, and the mixture was stirred under reflux for 3 hours.
Toluene was distilled off under reduced pressure, and 0.96 g of 4-phenyl-2-cyanomethylthiazole and 10 ml of tetrahydrofuran were added to the residue, followed by stirring under ice cooling. 0.25 g of sodium hydride was slowly added thereto, followed by stirring at room temperature overnight.
The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain crystals. The crystals were washed with isopropyl ether to obtain 1.4 g of the desired product (melting point: 168-169)
° C).

Synthesis Example 10 Synthesis of 2- (4-tert-butylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-dimethylaminoacrylonitrile (Compound No. 10) Synthesis 1) 4.7 g of 1-methyl-3,5-dichloropyrazole-4-carboxydimethylamide was dissolved in 30 ml of 1,4-dioxane, 5.2 g of Lawesson's reagent was added, and the mixture was stirred while heating under reflux for 4 hours. After cooling to room temperature and evaporating the solvent under reduced pressure, 100 ml of a dilute aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was sufficiently washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, n-hexane /
Ethyl acetate = 2/1) to give 1-methyl-3,5-
4.3 g of dichloropyrazole-4-carboxydimethylthioamide were obtained.

2) 1.0 g of 1-methyl-3,5-dichloropyrazole-4-carboxydimethylthioamide was dissolved in 5 ml of methanol, 1.2 g of methyl iodide was added, and the mixture was stirred under reflux for 1 hour. The methanol was distilled off, and the residue was 4-tert-butylphenylacetonitrile 0.3%.
Add 5 g and 10 ml of dimethylformamide at -40 ° C.
And cooled. 0.18 g of sodium hydride was added thereto, and the temperature was slowly raised to room temperature, followed by stirring at room temperature for 2 hours.
The reaction solution was poured into ice water, extracted with diethyl ether, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate = 2/1) to obtain 0.66 g of the desired compound (EZ) Mixture major / m
inor = 4/1). ¹ H-NMR (CDCl3, δ ppm) major: 1.24 (9H, s), 3.11 (6H, s), 3.69 (3H, s), 7.07-7.13 (2
H, m), 7.29-7.36 (2H, m) minor: 1.33 (9H, s), 2.69 (6H, s), 3.86 (3H, s), 7.07-7.13 (2
H, m), 7.29-7.36 (2H, m)

Synthesis Example 11 2- (2-tert-butylthiazol-4-yl) -3- (1-methyl-3,5
Synthesis of -dichloropyrazol-4-yl) -3-dimethylaminoacrylonitrile (Compound No. 11) The above compound was synthesized in the same manner as in Synthesis Example 10. ¹ H-NMR (CDCl3, δppm) 1.19 (9H, s), 3.16 (6H, s), 3.74 (3H, s), 6.94 (1H, s)

Synthesis Example 12 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-
Methyl-3,5-dichloropyrazol-4-yl) -3
-Dimethylaminoacrylonitrile (compound No. 1)
Synthesis of 2) The above compound was synthesized in the same manner as in Synthesis Example 10 (E / Z mixture major / minor = 9/1). ^{1 H-NMR (CDCl3, δppm} ) major: 3.20 (6H, s), 3.71 (3H, S), 6.42 (1H, m), 6.88-7.27 (3
H, m), 7.54 (1H, d, J = 2.6Hz) minor: 2.71 (6H, s), 3.90 (3H, s), 6.65 (1H, m), 6.88-7.27 (3
H, m), 7.80 (1 (E / Z mixture major / minor = 3/2) H, d, J =
2.6Hz)

[Synthesis Example 13] 2- ｛2- (piperazine-
Synthesis of 1-yl) thiazol-4-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-dimethylaminoacrylonitrile (Compound No. 13) Method similar to Synthesis Example 10. (E / Z mixture major / minor = 2/1). ¹ H-NMR (CDCl3, δppm) major: 1.56-1.68 (6H, m), 3.11 (6H, s), 3.16 (4H, m), 3.77 (3
H, s), 6.31 (1H, s) minor: 1.56-1.68 (6H, m), 2.84 (6H, s), 3.46 (4H, m), 3.81 (3
H, s), 6.38 (1H, s)

Synthesis Example 14 2- (2-tert-butylthiazol-4-yl) -3- (1-methyl-3,5
Synthesis of -dichloropyrazol-4-yl) -3-diallylaminoacrylonitrile (Compound No. 14) The above compound was synthesized in the same manner as in Synthesis Example 10 (E / Z mixture major / minor = 3/2). ¹ H-NMR (CDCl3, δ ppm) major: 1.20 (9H, s), 3.73 (3H, s), 4.02-4.06 (4H, m), 5.15
5.28 (4H, m), 5.73-5.85 (2H, m), 6.98 (1H, s) minor: 1.45 (9H, s), 3.63-3.64 (4H, m), 3.87 (3H, s), 5.15-
5.28 (4H, m), 5.73-5.85 (2H, m), 7.11 (1H, s)

Synthesis Example 15 2- (2-tert-butylthiazol-4-yl) -3- (2,4-dimethylthiazol-5-yl) -3-dimethylaminoacrylonitrile (Compound No. 15) The above compound was synthesized in the same manner as in Synthesis Example 10 (E / Z mixture major / minor = 2/1). ¹ H-NMR (CDCl3, δ ppm) major: 1.19 (9H, s), 2.07 (3H, s), 2.63 (3H, s), 3.16 (6H, s),
6.94 (1H, s) minor: 1.45 (9H, s), 2.48 (3H, s), 2.73 (3H, s), 2.78 (6H, s),
7.09 (1H, s)

[Synthesis Example 16] 2- {4- (2-fluorophenyl) -thiazol-2-yl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-dimethylamino Synthesis of Acrylonitrile (Compound No. 16) The above compound was synthesized in the same manner as in Synthesis Example 10 (EZ mixture). ¹ H-NMR (CDCl3, δ ppm) 3.25 (6H, s), 3.75 (1.5H, s), 3.90 (1.5H, s), 7.05-7.38 (3H,
m), 7.40 (0.5H, d) 7.42 (0.5H, d), 7.85 (1H, m)

Synthesis Example 17 2- (4-phenylthiazol-2-yl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-thiolacrylonitrile (Compound No. 17) Synthesis of 2- (4-phenylthiazol-2-yl) -3- (1
-Methyl-3,5-dichloropyrazol-4-yl)-
1.0 g of 3-trifluoromethanesulfonyloxyacrylonitrile was dissolved in 20 ml of dimethylformamide, 20 ml of a sodium hydrogen sulfide solution was added dropwise under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, n-hexane / ethyl acetate = 1/1).
Purification in 1) gave 0.45 g of the desired compound. ^{1 H-NMR (CDCl3, δppm} ) 4.05 (3H, s), 7.05-7.48 (6H, m)

Synthesis Example 18 2- (4-phenylthiazol-2-yl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-pivaloylthioacrylonitrile (compound NO. Synthesis of 18) 2- (4-phenylthiazol-2-yl) -3- (1
-Methyl-3,5-dichloropyrazol-4-yl)-
Dissolve 0.40 g of 3-thiolacrylonitrile and 0.21 g of triethylamine in 20 ml of chloroform,
Under ice cooling, 0.14 g of pivalic acid chloride was added dropwise, and the mixture was stirred at room temperature overnight. . The reaction solution was poured into ice water, extracted with chloroform, and washed with a small amount of water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, n-hexane / ethyl acetate = 3).
/ 1) to give 0.40 g of the desired compound. (Melting point: 185-186 ° C)

[Preparation Examples] Next, preparation examples of pest control agents containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples, "parts" means parts by weight.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 1 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shiono The above is uniformly mixed and pulverized into a wettable powder.

[Formulation Example 2] Emulsion The present compound No. 15 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) And

[Formulation Example 3] Suspending agent (flowable agent) 125 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd.) Xanthan gum 0.2 Part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

[Formulation Example 4] Water dispersible granule (dry flowable) 1 75 parts Hytenol NE-15 5 parts (anionic surfactant: Daiichi Kogyo Pharmaceutical Co., Ltd.) Vanirex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (Synthetic hydrous silicic acid: trade name of Shionogi & Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring and mixing, granulating with an extruder, drying and granulating water. It should be a sum.

[Formulation Example 5] Granules Compound of the present invention 15 parts 50 parts bentonite 45 parts talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and mixed, and the mixture is granulated by an extrusion granulator and dried to obtain granules.

[Formulation Example 6] Powder Compound No. 13 parts Carplex # 80D 0.5 part (Synthetic hydrated silica: trade name of Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to obtain a powder.

For use, the above-mentioned wettable powder, emulsion, flowable and granular wettable powder are diluted 50 to 20,000 times with water to obtain an active ingredient of 0.005 to 0.005 per hectare (ha).
Spray to 50kg.

Test Examples Next, the usefulness of the compound of the present invention as a pesticidal agent will be specifically described in the following test examples.

[Test Example 1] Insecticidal test against leafhopper leafhopper Rice foliage was immersed in a 1000 ppm emulsified solution of the compound of the present invention for about 10 seconds, and the foliage was put into a glass cylinder.
Release the adult leafhopper, which shows resistance to the organophosphorus insecticide, cover it with a perforated lid, and store it in a constant temperature room at 25 ° C.
The number of dead insects after 6 days was investigated, and the mortality was calculated from the same formula as in Test Example 1. Note that the test was performed in a two-section system. As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention no. : 15,18

[Test Example 2] Insecticidal test against peach aphid Moth filter paper was spread on a glass petri dish having an inner diameter of 3 cm, and cabbage leaves of the same diameter were placed thereon. Four wingless adult female peach aphids were released, and one day later, a chemical solution was sprayed (2.5 mg / cm 2) using a rotary spray tower. The drug solution was prepared by diluting a 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) with water containing a spreading agent.
The one adjusted to a concentration of 000 ppm was used. Six days after the treatment, the mortality of adults and larvae was determined by the following formula. The test was performed in two sections.

Mortality (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100 As a result, the following compounds showed a mortality of 80%. The compound of the present invention no. : 3,15,18

Test Example 3 Contact Insecticidal Test Against Japanese Diamondback Persimmon leaves were immersed in a 1000 ppm aqueous emulsion of the compound of the present invention for about 10 seconds, air-dried and placed in a petri dish.
The second instar larva was released into the petri dish at a rate of 10 per petri dish, covered with a perforated lid and housed in a thermostat at 25 ° C. The number of dead insects after 6 days was investigated, and the same formula as in Test Example 1 was used. Mortality was determined. Note that the test was performed in a two-section system. As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention no. : 2,18

[Test Example 4] Insecticidal test against rice beetle 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent. , The cucumber leaf was immersed in this solution for about 10 seconds, air-dried and placed in a petri dish, into which 10 larvae of the second instar larvae of burs beetle were released per petri dish, and covered. The mortality after 6 days was stored in a constant temperature room at 25 ° C., and the mortality was calculated from the same formula as in Test Example 1. The test was performed in two sections.

As a result, the following compounds exhibited 100% mortality. The compound of the present invention no. : 10, 11, 12, 14, 17,
18

[0209]

The present invention provides a novel insecticide having low toxicity and low residue.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/50 A01N 43/50 43/54 43/54 43/56 43/56 43/58 43/58 43/60 43/60 43/647 43/647 43/653 43/653 43/66 43/66 43/707 43/707 43/713 43/713 43/78 43/78 43/80 43/80 43/82 43/82 47 / 04 47/04 47/28 47/28 C07D 213/57 C07D 213/57 231/16 231/16 235/16 235/16 261/08 261/08 263/32 263/32 263/56 263/56 271 / 06 271/06 271/10 271/10 275/02 275/02 275/03 277/30 277/30 277/34 277/34 307/54 307/54 333/28 333/28 401/04 231 401/04 231 401/14 231 401/14 231 417/06 231 417/06 231 275/02 (72) Inventor Yoshihide Masawa 722-1, Tsuboi-cho, Funabashi-shi, Chiba Pref. Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Invention Toshio Miyake 1470 Shirooka, Shiraoka-cho, Minamisaitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd. In the laboratory (72) Inventor Yoichi Inoue 1470, Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Nissan Chemical Industry Co., Ltd. In the laboratory (72) Inventor Shinji Takii 1470 Shirooka, Shirooka-cho, Minamisaitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd.

Claims (6)

[Claims] (1) Formula (1):Wherein Q is phenyl optionally substituted with G, G
Optionally substituted with naphthyl or R
Optionally a heterocyclic group (however, this heterocyclic group
, Furyl, pyrrolyl, oxazolyl, isoxazoly
, Thiazolyl, isothiazolyl, pyrazolyl, imida
Zolyl, 1,3,4-oxadiazolyl, 1,2,4-
Oxadiazolyl, 1,3,4-thiadiazolyl, 1,
2,4-thiadiazolyl, 1,2,4-triazolyl,
1,2,3-thiadiazolyl, 1,2,3-triazolyl
1,2,3,4-tetrazolyl, pyridinyl, pyri
Midinyl, pyrazinyl, pyridazinyl, 1,3,5-to
Riadinyl, 1,2,4-triazinyl, 1,2,4
5-tetrazinyl, pyrazolinyl, imidazolinyl, e
Xazozolinyl, isoxazolinyl, thiazolinyl, imi
Dazolinone, imidazolidinedione, 3 (2H) -pyri
Dazinone, benzothiazolyl, benzimidazolyl, a
Ndazolyl, benzoxazolyl, quinolinyl, isoki
Nolinyl, quinoxalinyl, phthalazinyl, cinnolini
Or quinazolinyl. B is halogen, S (O) nL¹Or NL^TwoL^ThreeIn
A is phenyl optionally substituted with W;
May be substituted by naphthyl or Y
Heterocyclic groups (provided that the heterocyclic groups are thienyl,
, Pyrrolyl, oxazolyl, isoxazolyl, thiazo
Ryl, isothiazolyl, pyrazolyl, imidazolyl,
1,3,4-oxadiazolyl, 1,2,4-oxadi
Azolyl, 1,3,4-thiadiazolyl, 1,2,4-
Thiadiazolyl, 1,2,4-triazolyl, 1,2,2
3-thiadiazolyl, 1,2,3-triazolyl, 1,
2,3,4-tetrazolyl, pyridinyl, pyrimidiny
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, pyrazolinyl, imi
Dazolinyl, oxazolinyl, isoxazolinyl, thia
Zolinyl, 3 (2H) -pyridazinone, benzothiazoly
, Benzimidazolyl, indazolyl, benzoxa
Zolyl, quinolinyl, isoquinolinyl, quinoxalini
, Phthalazinyl, cinnolinyl or quinazolinyl
is there. ), Where (a) B is NL^TwoL^ThreeAnd Q is replaced by R
1,2,3,4-tetrazolyl, optionally substituted with R
Optionally substituted with quinolyl or R
In the case of isoquinolyl, A is substituted by W
Or a heterocyclic ring optionally substituted by Y
Groups (this heterocyclic group can be thienyl, furyl, pyrrolyl,
Sazolyl, isoxazolyl, thiazolyl, isothiazoly
, Pyrazolyl, imidazolyl, 1,3,4-oxadi
Azolyl, 1,2,4-oxadiazolyl, 1,3,4
Thiadiazolyl, 1,2,4-thiadiazolyl, 1,
2,4-triazolyl, 1,2,3-thiadiazolyl,
1,2,3-triazolyl, pyridinyl, pyrimidiny
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, pyrazolinyl, imi
Dazolinyl, oxazolinyl, isoxazolinyl, thia
Zolinyl, 3 (2H) -pyridazinone, benzothiazoly
, Benzimidazolyl, indazolyl, benzoxa
Zolyl, quinolinyl, isoquinolinyl, quinoxalini
, Phthalazinyl, cinnolinyl or quinazolinyl
is there. (B) B is S (O) nL¹And Q is replaced by R
A is substituted with W in the case of benzothiazolyl which may be
Optionally substituted phenyl, optionally substituted with W
A heterocyclic group optionally substituted by naphthyl or Y (this
Heterocyclic groups are thienyl, furyl, pyrrolyl, oxazolyl
, Isoxazolyl, thiazolyl, isothiazolyl,
Lazolyl, imidazolyl, 1,2,4-triazolyl,
1,2,3-triazolyl, 1,2,3,4-tetrazo
Lil, pyridinyl, pyrimidinyl, pyrazinyl, pyrida
Zinyl, 1,3,5-triazinyl, 1,2,4-tri
Azinyl, pyrazolinyl, imidazolinyl, oxazoly
Nil, isoxazolinyl, thiazolinyl, 3 (2H)-
Pyridazinone, benzothiazolyl, benzimidazoli
, Indazolyl, quinolinyl, isoquinolinyl, quino
Xalinyl, phthalazinyl, cinnolinyl or quinazo
Linyl. (C) B is halogen, S (O) nL¹Or NL^TwoL^ThreeIn
And Q is phenyl optionally substituted with G
Is such that A is naphthyl or Y optionally substituted by W
An optionally substituted heterocyclic group (this heterocyclic group is
, Oxazolyl, isoxazolyl, thiazolyl, iso
Thiazolyl, pyrazolyl, 1,3,4-oxadiazoli
1,2,4-oxadiazolyl, 1,3,4-thia
Diazolyl, 1,2,4-thiadiazolyl, 1,2,4
-Triazolyl, 1,2,3-thiadiazolyl, 1,
2,3-triazolyl, 1,2,3,4-tetrazoli
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, pyrazolinyl, imi
Dazolinyl, oxazolinyl, isoxazolinyl, thia
Zolinyl, 3 (2H) -pyridazinone, benzothiazoly
, Benzimidazolyl, indazolyl, benzoxa
Zolyl, quinoxalinyl, phthalazinyl, cinnolinyl
Or quinazolinyl. ) And L¹Is H, C₁~ C_FourAlkyl, C_Two~_FourAlkenyl, C_Two
~_FourAlkynyl, C₁~ C_ThreeEven if substituted with alkyl
Good C_Three~ C₆Cycloalkyl, C₁~ C_FourHaloalkyl,
CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, Replaced by Z
Optionally phenyl, C substituted with Ra₁~ C_FourArchi
, C substituted with Rb₁~ C_FourAlkyl, tetrahydro
Pyranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfe
Nil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourArchi
Rusulfonyl, halogen or C₁~ C_FourAlkyl
Optionally substituted phenylsulfenyl and halogen
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Rusulfinyl, halogen or C₁~ C_FourWith alkyl
Optionally substituted phenylsulfonyl, -SO _TwoC
F_Three, C₁~ C_FourMonoalkylaminosulfonyl, C_Two~ C
₈Dialkylaminosulfonyl, phenylaminosulfo
Nil, C_Two~ C_FiveMonoalkylaminothiocarbonyl, C
_Three~ C₉Dialkylaminothiocarbonyl, C_Two~ C_FiveSheer
Noalkyl, C _Three~ C₉Alkoxycarbonylalkyl,
-C (O) T¹, -P (O) T^TwoT^Three, -P (S) T
^TwoT^Three, Alkali metal, alkaline earth metal or NHT^FourT
^FiveT⁶And L^TwoAnd L^ThreeAre each independently H, C₁~ C_FourAlkyl, C
_Two~ C_FourAlkenyl, C _Two~ C_FourAlkynyl, C₁~ C_ThreeAl
C optionally substituted with a kill group_Three~ C₆Cycloalkyl
Le, C₁~ C_FourHaloalkyl, C_Two~ C_FourAlkoxyalkyl
Le, CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, Replaced by Z
Optionally substituted phenyl, C substituted with Ra₁~ C_FourA
Alkyl, C substituted with Rb₁~ C_FourAlkyl, tetrahi
Dropyranil, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsul
Honyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally phenylsulfonyl, -SO_TwoCF_Three, C₁
~ C_FourMonoalkylaminosulfonyl, C_Two~ C₈Gials
Killaminosulfonyl, phenylaminosulfonyl, C
_Two~ C_FiveMonoalkylaminothiocarbonyl, C_Three~ C₉The
Alkylaminothiocarbonyl, C_Two~ C_FiveCyano Archi
Le, C_Three~ C₉Alkoxycarbonylalkyl, -C
(O) T¹, -P (O) T^TwoT^Three, -P (S) T^TwoT^Three,
Lucari metal, alkaline earth metal or NHT^FourT^FiveT⁶so
Or L^TwoAnd L^ThreeIs the combined nitrogen
Including oxygen, nitrogen or sulfur atoms
G may form a 5- to 8-membered ring group which may have₁~ C_TenAlkyl, C_Two~ C_FourCyano
Alkyl, C substituted with Ra₁~ C_FourAlkyl, C_Two~ C
₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloal
Kill, C_Two~ C₆Haloalkenyl, C_Two~ C₆Halo alkini
Le, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeWith alkyl
Optionally substituted C_Three~ C₆Cycloalkyl, C₁~
C_TenAlkoxy, C_Two~ C₆Alkenyloxy, C_Two~ C₆
Alkynyloxy, C₁~ C_FourHaloalkoxy, C_Two~ C₆
Haloalkenyloxy, C_Two~ C₆Haloalkynyloxy
Si, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkyl
Sulfinyl, C₁~ C_FourAlkylsulfonyl, C_Two~ C₆
Alkenylsulfenyl, C_Two~ C₆Alkenyl sulphie
Nil, C_Two~ C₆Alkenylsulfonyl, C_Two~ C₆Archi
Nilsulfenyl, C_Two~ C₆Alkynylsulfinyl,
C_Two~ C₆Alkynylsulfonyl, C₁~ C_FourHaloalkyl
Sulfenyl, C₁~ C_FourHaloalkylsulfinyl, C
₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆Haloalkene
Rusulfenyl, C_Two~ C₆Haloalkenylsulfini
Le, C_Two~ C₆Haloalkenylsulfonyl, C_Two~ C₆Halo
Alkynylsulfenyl, C_Two~ C₆Haloalkynylsul
Finil, C_Two~ C₆Haloalkynylsulfonyl, CH
O, NO_Two, CN, -NU¹U^Two, OH, naphthyl, Ra
Substituted methoxy, C_Two~ C₇Alkoxycarbonyl,
C_Two~ C _FourAlkoxyalkyl, C_Two~ C_FourAlkyl carb
Nil, C_Two~ C_FourHaloalkylcarbonyl, C_Two~ C_FiveAl
Kill carbonyloxy, C_Two~ C_FiveHaloalkylcarboni
Luoxy, C_Three~ C₇Dialkylaminocarbonyloxy
C, phenyl optionally substituted with Z, substituted with Z
Phenoxy, which may be substituted with Z
Nzoyl, pyridyl optionally substituted with Z,
Optionally substituted pyridyloxy, substituted with Z
Thienyl, methyle bonded at adjacent substitution positions
Dioxy, halomethylene linked at adjacent substitution positions
Dioxy and -N = CT⁷T⁸(However, T⁷And T⁸Are each
Independently, H, phenyl, benzyl or C₁~ C₆Archi
Or T⁷And T⁸Together with the carbon atom to which
It may form a 5- to 8-membered ring. ) Selected from
1 to 4 substituents or bonding at adjacent substitution positions
A 5- to 8-membered ring formed by an alkylene group
R is halogen, C₁~ C_TenAlkyl, substituted by Ra
C₁~ C_FourAlkyl, C _Two~ C₆Alkenyl, C_Two~ C₆A
Lucinyl, C₁~ C₆Haloalkyl, C_Two~ C₆Halo arche
Nil, C_Two~ C₆Haloalkynyl, C_Three~ C₆Halocycloa
Luquil, C₁~ C_ThreeC optionally substituted with alkyl_Three
~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C_Two~ C₆
Alkenyloxy, C_Two~ C₆Alkynyloxy, C₁~
C_FourHaloalkoxy, C_Two~ C₆Haloalkenyloxy,
C_Two~ C₆Haloalkynyloxy, C ₁~ C_FourAlkylsul
Phenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourA
Rukylsulfonyl, C_Two~ C₆Alkenylsulfenyl,
C_Two~ C₆Alkenylsulfinyl, C_Two~ C₆Alkenyl
Sulfonyl, C_Two~ C₆Alkynylsulfenyl, C_Two~
C₆Alkynylsulfinyl, C_Two~ C₆Alkynyls
Ruphonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~
C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkyl
Sulfonyl, C_Two~ C₆Haloalkenylsulfenyl, C
_Two~ C₆Haloalkenylsulfinyl, C_Two~ C₆Haloal
Kenylsulfonyl, C_Two~ C₆Haloalkynylsulfeni
Le, C_Two~ C₆Haloalkynylsulfinyl, C_Two~ C₆C
Loalkynylsulfonyl, NO_Two, CN, -NU¹U^Two,
Phenoxy, OH, naphthyl, C_Two~ C₇Alkoxycal
Bonil, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FourArchi
Lecarbonyl, C_Two~ C_FiveAlkylcarbonyloxy, C
_Two~ C_FiveHaloalkylcarbonyloxy, substituted with X
Benzoyl, optionally substituted with X
Nil, pyridyl optionally substituted by X, substituted by X
Optionally thienyl and -N = CT⁷T⁸Choose from
1 to 4 substituents or adjacent substitution positions
5 to 8 formed by an alkylene group linked by
Y is halogen, C₁~ C_TenAlkyl, C₁~ C₆Haloa
Luquil, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy
Si, C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Haloal
Quinyloxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C_Two~ C₆Alkenylsulfenyl, C_Two~ C₆Arche
Nilsulfinyl, C_Two~ C₆Alkenylsulfonyl, C
_Two~ C₆Alkynylsulfenyl, C _Two~ C₆Alkynyls
Rufinil, C_Two~ C₆Alkynylsulfonyl, C₁~ C_Four
Haloalkylsulfenyl, C₁~ C_FourHaloalkylsul
Finil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆
Haloalkenylsulfenyl, C_Two~ C₆Haloalkenyl
Sulfinyl, C_Two~ C₆Haloalkenylsulfonyl, C
_Two~ C₆Haloalkynylsulfenyl, C_Two~ C₆Haloal
Quinylsulfinyl, C_Two~ C₆Haloalkynylsulfoni
Le, NO_Two, CN, -NU¹U^Two, OH, C_Two~ C₇Alkoki
Cicarbonyl, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_Five
Alkylcarbonyloxy, C_Two~ C_FiveHaloalkylcal
Bonyloxy, C_Three~ C₇Dialkylaminocarbonylo
Xy, phenyl optionally substituted with X, and -N =
CT⁷T⁸(However, T⁷And T⁸Are each independently H, phenyl
Benzyl, or C₁~ C₆Alkyl or T⁷When
T⁸And a 5- to 8-membered ring together with the carbon atom to which
It may be formed. ) 1 to 4 positions selected from
Or an alkylene group bonded at an adjacent substitution position
W is a halogen, C is a 5- to 8-membered ring formed by₁~ C₆Alkyl, C₁~ C_FourHaloal
Kill, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy,
C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHalo
Alkylsulfenyl, C₁~ C_FourHaloalkyl sulfy
Nil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C_FourAl
Kenil, C_Two~ C_FourHaloalkenyl, C_Two~ C_FourAlkenyl
Oxy, C_Two~ C_FourHaloalkenyloxy, C_Two~ C_FourAl
Kenylsulfenyl, C_Two~ C_FourAlkenylsulfini
Le, C_Two~ C_FourAlkenylsulfonyl, C_Two~ C_FourHaloal
Kenylsulfenyl, C_Two~ C_FourHaloalkenyl sulphie
Nil, C_Two~ C_FourHaloalkenylsulfonyl, C_Two~ C_FourA
Lucinyl, C_Two~ C_FourHaloalkynyl, C_Two~ C_FourAlkini
Luoxy, C_Two~ C_FourHaloalkynyloxy, C_Two~ C_FourA
Ruquinylsulfenyl, C_Two~ C_FourAlkynyl sulfini
Le, C_Two~ C_FourAlkynylsulfonyl, C_Two~ C_FourHaloal
Quinylsulfenyl, C_Two~ C_FourHaloalkynyl sulfy
Nil, C_Two~ C_FourHaloalkynylsulfonyl, NO_Two, C
N, formyl, C_Two~ C₆Alkoxycarbonyl, C_Two~
C₆Alkylcarbonyl, C_Two~ C₆Haloalkylcarbo
Nil, C_Two~ C₆Alkylcarbonyloxy and -NU¹
U^Two1 to 5 substituents selected from¹Is hydrogen, C₁~ C₂₀Alkyl, C_Two~ C₆Alkene
Le, C₁~ C₆Haloalkyl, C₁~ C_FourAlkoxy-C₁
~ C_FourAlkyl, C_Three~ C₆Halocycloalkyl, substituted with Ra
Transformed C₁~ C_FourAlkyl, C₁~ C_ThreeSubstituted with alkyl
C that may be_Three~ C₆Cycloalkyl, substituted with Ra
Cycloalkyl, Ra and C₁~ C_FourSubstitute with alkyl
Substituted with substituted cyclopropyl, Rc and halogen
C_Three~ C_FourCycloalkyl group, Rd and C₁~ C_FourAlkyl
A cyclopropyl group substituted with Ra, a C substituted with Ra_Two~
C_FourAlkenyl, C₁~ C₁₂Alkoxy, C₁~ C_FourHaloa
Lucoxy, C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeArchi
C optionally substituted with_Three~ C₆Cycloalkoxy,
Benzyloxy, C_Two~ C_FiveAlkoxycarbonyl, -N
U¹U^Two, Phenylamino, a group optionally substituted with Z
Phenyl, phenoxy optionally substituted with Z,
Optionally substituted phenylthio, substituted with Z
Or a heterocyclic ring optionally substituted by Z
Groups (however, these heterocyclic groups are thienyl, furyl, pyro
Ryl, oxazolyl, isoxazolyl, thiazolyl, i
Sothiazolyl, pyrazolyl, imidazolyl, 1,3,4
-Oxadiazolyl, 1,2,4-oxadiazolyl,
1,3,4-thiadiazolyl, 1,2,4-thiadiazo
Ryl, 1,2,4-triazolyl, 1,2,3-thiazi
Azolyl, 1,2,3-triazolyl, 1,2,3,4
-Tetrazolyl, pyridinyl, pyrimidinyl, pyrazini
, Pyridazinyl, 1,3,5-triazinyl, 1,
2,4-triazinyl, pyrazolinyl, imidazolini
Oxazolinyl, isoxazolinyl, thiazolinyl
And 3 (2H) -pyridazinone. )so
Yes, T^TwoAnd T^ThreeIs independently OH, phenyl, C₁~ C₆
Alkyl, C₁~ C₆Alkoxy or C₁~ C_FourAlkyl
Sulfphenyl, T^Four, T^FiveAnd T⁶Are each independently H, C₁~ C₆Archi
Le, C₁~ C₆Alkenyl, C₁~ C_ThreeSubstituted with an alkyl group
C that may be_Three~ C₆Cycloalkyl group or benzyl
Or T^Four, T^FiveAnd T⁶Two of
Is an oxygen atom together with the nitrogen atom to which each is attached,
5 not containing nitrogen or sulfur atoms
X and Z are each independently halogen, C₁~ C_FourArchi
Le, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁
~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulfeni
Le, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkyl
Sulfonyl, C_Two~ C_FiveAlkenylsulfenyl, C_Two~
C_FiveAlkenylsulfinyl, C_Two~ C_FiveAlkenyl sulf
Honyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_Four
Haloalkylsulfinyl, C₁~ C_FourHaloalkylsul
Honyl, NO_Two, CN, CHO, OH, -NU¹U^Two,
Phenyl, phenoxy and C_Two~ C_FiveAlkoxycarbonyl
1 to 5 substituents selected from⁷And T⁸Are each independently H, phenyl, benzyl or
Or C₁~ C₆Alkyl or T⁷And T⁸When
Forms a 5- to 8-membered ring with the carbon atom to which they are attached
May be U¹And U^TwoIs independently H, C₁~ C₆Alkyl, C
_Two~ C_FiveAlkylcarbonyl, phenyl or benzyl
Represent or U¹And U^TwoTogether with the carbon atom to which it is bound
N may be 0, 1 or 2; Ra is halogen and C₁~ C_Four1 selected from alkyl
Rb is halogen and C₁~ C_Four1 selected from alkyl
Rc is halogen and C₁~ C_FourSelected from alkoxy
Rd is a phenyl optionally substituted with one or more halogens,_Two~ C_FourAlkene
It is. An acrylonitrile compound represented by the formula: 2. The acrylonitrile compound according to claim 1, wherein Q is phenyl optionally substituted with G, thiazolyl optionally substituted with R, or pyrazolyl optionally substituted with R. 3. The acrylonitrile compound according to claim 1, wherein Q is phenyl optionally substituted with G. 4. The acrylonitrile compound according to claim 1, wherein Q is thiazolyl optionally substituted with R. 5. The acrylonitrile compound according to claim 1, wherein Q is pyrazolyl optionally substituted with R. 6. An agricultural chemical comprising at least one of the acrylonitrile compounds according to claim 1 as an active ingredient.